Methods of removing color from color-treated hair

ABSTRACT

The disclosure relates to compositions and methods for removing direct dyes from hair, the methods comprising contacting hair with a composition comprising at least one organic salt selected from imidazolium-based compounds and/or ammonium-based compounds.

FIELD OF THE DISCLOSURE

The present disclosure generally relates to compositions for use inremoving color from color-treated or pre-dyed hair and methods ofremoving color from color-treated or pre-dyed hair, and moreparticularly using organic salts to remove direct dyes fromcolor-treated or pre-dyed hair.

BACKGROUND

The process of changing the color of hair can involve depositing anartificial color onto the hair which provides a different shade or colorto the hair, and/or lifting the color of the hair, such as lighteningthe color of dark hair to lighter shades.

Imparting a color change or color effect on hair can be done usingpermanent, semi-permanent, or temporary hair coloring products.Semi-permanent dyeing uses direct dyes, which are nonionic or ionic dyesand colored compounds capable of producing a more or less pronouncedchange of the natural color of the hair. These dyes may or may not beused in the presence of an oxidizing agent. In contrast with oxidationdye precursors, a direct dye is a relatively large molecule that doesnot penetrate easily into the core of the fiber. Nevertheless, such dyescan be resistant to shampoo-washing, even after several washes.

However, many consumers desire to quickly change hair color. That is,they wish to dye the hair a particular color and then change to anothercolor before the first color has naturally washed out, and thus must usea color removal product. Most color removal products in the currentcosmetic market are based on destroying dyes placed in or on the hair bymeans of oxidative or reductive reactions. However, those approacheshave significant drawbacks of damaging hair fibers. Thus, there is adesire to provide ways to accelerate the removal of direct dyes fromcolor-treated hair, and particularly without damaging the hair.

SUMMARY OF THE DISCLOSURE

One aspect of the disclosure pertains to a method of removing one ormore direct dye(s) from hair. In one or more embodiments, the methodcomprises:

-   -   a. contacting hair with a composition comprising:        -   i. an organic salt selected from:

an imidazolium-based compound having a structure represented by Formula(I) below:

-   -   wherein R1 and R2 are each independently a linear or branched        alkyl group having 1-16 carbon atoms, and X⁻ is selected from        halides, carboxylates, C₁₋₁₆ fatty acid carboxylates,        phosphates, phosphate derivatives, tosylates, tosylate        derivatives, sulfates or sulfate derivatives,

an ammonium-based compound having a structure represented by Formula(II) below:

-   -   wherein R1, R2, R3 and R4 are each independently a saturated or        unsaturated, linear, branched or cyclic group with a carbon        chain length of C₁₋₂₀, and optionally substituted by one or more        hydroxyl, amino C₁₋₄ radicals, alkylamino, carboxy, carboxylate,        carbamide, C₁₋₄ alkoxy, —SO₃H, sulfonate or aryl, and X⁻ is        selected from halides, carboxylates, C₁₋₁₆ fatty acid        carboxylates, phosphates, phosphate derivatives, tosylates,        tosylate derivatives, sulfates or sulfate derivatives, and

a combination thereof; and

-   -   b. rinsing the composition from the hair.

Another aspect of the disclosure pertains to a method of removing colorfrom or controlling the removal of color from or lightening the color ofhair, the method comprising:

-   -   a. contacting hair with a composition comprising the organic        salt of the present disclosure; and    -   b. rinsing the composition from the hair;        wherein the hair has been pre-dyed with one or more direct        dye(s).

Another aspect of the disclosure relates to the use of organic salts andto compositions containing organic salts, the salts being selected fromthe above-described imidazolium-based compounds and/or ammonium-basedcompounds in order to remove the one or more direct dyes fromcolor-treated hair or hair pre-dyed with the one or more direct dye(s).

In various embodiments, the hair has been pre-dyed with one or moredirect dye(s) having a positive Log P_(ow) value, such as a hydrophobicdirect dye, or one or more direct dye(s) having a negative Log P_(ow)value, such as a cationic direct dye, or one or more direct dye(s)having a neutral Log P_(ow) value, such as a nonionic direct dye, orcombinations thereof.

BRIEF DESCRIPTION OF THE FIGURES

FIG. 1 is a graphical representation of ΔE values of several dyed hairswatches treated with solutions containing various concentrations oforganic salts and evaluated for dye removal, as well as a control.

FIG. 2 is a graphical representation of ΔE values of dyed hair swatchestreated with water and two solutions, each containing a differentorganic salt.

FIG. 3 is a graphical representation of ΔE values of dyed hair swatchestreated with water and a solution containing an organic salt.

DETAILED DESCRIPTION OF THE DISCLOSURE

The present disclosure relates to a method of removing one or moredirect dye(s) from hair. In one or more embodiments, the methodcomprises:

a. contacting hair with a composition comprising:

-   -   i. an organic salt selected from:

an imidazolium-based compound having a structure represented by Formula(I) below:

-   -   wherein R1 and R2 are each independently a linear or branched        alkyl group having 1-16 carbon atoms, and X⁻ is selected from        halides, carboxylates, C₁₋₆ fatty acid carboxylates, phosphates,        phosphate derivatives, tosylates, tosylate derivatives, sulfates        or sulfate derivatives,

an ammonium-based compound having a structure represented by Formula(II) below:

-   -   wherein R1, R2, R3 and R4 are each independently a saturated or        unsaturated, linear, branched or cyclic group with a carbon        chain length of C₁₋₂₀, and optionally substituted by one or more        hydroxyl, amino C₁₋₄ radicals, alkylamino, carboxy, carboxylate,        carbamide, C₁₋₄ alkoxy, —SO₃H, sulfonate or aryl, and X⁻ is        selected from halides, carboxylates, C₁₋₁₆ fatty acid        carboxylates, phosphates, phosphate derivatives, tosylates,        tosylate derivatives, sulfates or sulfate derivatives, and

a combination thereof; and

b. rinsing the composition from the hair.

In some embodiments, R1, R2, R3 and R4 of the imidazolium-based compoundhaving a structure represented by Formula (I) are each independently alinear or branched alkyl group with a carbon chain length of C₁₋₂₀, andX⁻ of Formula (I) is selected from carboxylates, C₁₋₁₆ fatty acidcarboxylates, sulfates, or sulfate derivatives, including alkylsulfates.

In some embodiments, the organic salt comprises an imidazolium-basedcompound selected from butyl-3-methylimidazolium octyl sulfate,butyl-3-methylimidazolium acetate, ethyl-3-methylimidazoliumethylsulfate, 1-ethyl-3-ethyl imidazolium acetate,1-ethyl-3-methylimidazolium tosylate, and combinations thereof.

In some embodiments, the ammonium-based compound of Formula (II) isselected from:

wherein X⁻ of Formula (II) is selected from halides, carboxylates, C₁₋₁₆fatty acid carboxylates, phosphates, phosphate derivatives, tosylates,tosylate derivatives, sulfates or sulfate derivatives.

In an embodiment, the organic salt comprises an ammonium-based compoundcomprising a tributylmethyl ammonium salt, such as tributylmethylammonium chloride.

In an embodiment, the organic salt is selected frombutyl-3-methylimidazolium octyl sulfate, butyl-3-methylimidazoliumacetate, ethyl-3-methylimidazolium ethylsulfate, 1-ethyl-3-ethylimidazolium acetate, 1-ethyl-3-methylimidazolium tosylate,tributylmethyl ammonium chloride, or combinations thereof.

In various embodiments, the hair to be contacted with the hair treatmentor the hair color removal compositions of the present disclosure hasbeen pre-dyed with one or more direct dye(s) having a positive LogP_(ow) value, or one or more direct dye(s) having a negative Log P_(ow)value, or one or more direct dye(s) having a neutral Log P_(ow) value,or combinations thereof.

In various embodiments, the hair to be contacted with the hair treatmentor the hair color removal compositions of the present disclosure hasbeen pre-dyed with one or more direct dye(s) having a positive LogP_(ow) value.

In various embodiments, the hair to be contacted with the hair treatmentor the hair color removal compositions of the present disclosure hasbeen pre-dyed with one or more direct dye(s) having a positive LogP_(ow) value including at least one hydrophobic direct dye.

In one or more embodiments, the hydrophobic direct dye is selected fromHC blue 15, hydroxyanthraquinoneaminopropyl methyl morpholiniummethosulfate, Basic violet 2, Disperse violet 1, Disperse red 15,Disperse blue 3, Disperse blue 377, Disperse 99, Solvent violet 13,Basic blue 6, HC blue 16, Basic blue 99, HC blue 14, Basic brown 16,Acid green 25, Acid black 1, HC red 7, HC orange 2,3-Nitro-p-hydroxyethylaminophenol, Acid red 33, HC violet no.1,2-Nitro-5-glyceryl methylaniline, 3-Methylamino-4-nitrophenoxyethanol,4-Amino-3-nitrophenol, H yellow 9, Acid red 52, Acid orange 7, Acid red18, HC yellow no.7, Acid red 92, Acid violet 43, Ext violet 2, Acidgreen 25, Acid black 1, and combinations thereof.

In various embodiments, the hair to be contacted with the hair treatmentor the hair color removal compositions of the present disclosure hasbeen pre-dyed with one or more direct dye(s) having a negative LogP_(ow) value.

In various embodiments, the hair to be contacted with the hair treatmentor the hair color removal compositions of the present disclosure hasbeen pre-dyed with one or more direct dye(s) having a negative LogP_(ow) value including at least one cationic direct dye.

In one or more embodiments, the cationic direct dye is selected from thegroup consisting of basic orange 31, basic red 51, basic yellow 57, HCblue no.2, Acid yellow 23, Basic orange 31, Basic yellow 87, Acid yellow3, HC Red 3, Acid blue 9, Basic brown 17, and combinations thereof.

In various embodiments, the hair to be contacted with the hair treatmentor the hair color removal compositions of the present disclosure hasbeen pre-dyed with one or more direct dye(s) comprising at least onehydrophobic direct dyes and at least one cationic direct dye.

In some embodiments, the composition of the present disclosure furthercomprises at least one surfactant.

In some embodiments, the composition of the present disclosure can becombined with another composition containing at least one surfactantsuch as an anionic surfactant or a non-ionic surfactant. In some cases,the composition of the present disclosure can be combined with a shampoocomposition containing an anionic surfactant.

Suitable examples of the surfactant include anionic surfactants such asalkyl(ether) sulfates, alkyl sulfates, alkenyl ether sulfates, alkenylsulfates, sulfosuccinates, sarcosinates, isethionates, and combinationsthereof. For example, the anionic surfactants may be chosen from sodiumlaureth sulfate, ammonium capryleth sulfate, ammonium pareth-25 sulfate,ammonium myreth sulfate, ammonium laureth sulfate, sodium decyl ethersulfate, sodium lauryl sulfate, sodium dodecyl sulfate, ammonium laurylsulfate, disodium laureth sulfosuccinate, diethylhexyl sodiumsulfosuccinate, dioctyl sodium sulfosuccinate, sodium cocoylisethionate, sodium methy; isethionate, sodium oleoyl isethionate,sodium lauroyl methyl isethionate, sodium cocoyl methyl isethionate,sodium oleoyl methyl isethionate, sodium N-lauroyl sarcosinate, disodiumlaureth sulfosuccinate, and combinations thereof.

Other suitable examples of the surfactant include amphoteric surfactantssuch as alkyl betaines, alkyl amido betaines, alkylampho(di)acetates,alkylamphopropionates, and alkanolamides. Examples of amphotericsurfactants are cocamidopropyl betaine, coco-betaine, Sodiumcocoamphopropionate, and combinations thereof.

Suitable examples of the surfactant include nonionic surfactants such asalkylpolyglucosides. Examples of alkylpolyglucosides are decylglucoside, coco-glucoside, cetearyl glucoside, and lauryl glucoside.

In one or more embodiments, the surfactant comprises anionic surfactantsselected from sodium lauryl sulfate, sodium laureth sulfate, sodiumdodecyl sulfate, ammonium lauryl sulfate, ammonium laureth sulfate, andcombinations thereof.

In one or more embodiments, the surfactant comprises alkylpolyglucosidesselected from decyl glucoside, coco-glucoside, lauryl glucoside,cetearyl glucoside, and combinations thereof.

In an embodiment, the composition of the present disclosure is a shampoocomposition containing at least one anionic surfactant.

In various embodiments, the one or more direct dye(s) is a direct dyehaving a positive Log P_(ow) value, or a direct dye having a negativeLog P_(ow) value, or a direct dye having a neutral Log P_(ow) value, orcombinations thereof.

In an embodiment, the methods of the present disclosure are utilized foraccelerating the removal of certain direct dyes, such as hydrophobicdirect dyes or dyes having a positive Log P_(ow) value from hair.

In some embodiments, the organic salt is selected frombutyl-3-methylimidazolium octyl sulfate, butyl-3-methylimidazoliumacetate, ethyl-3-methylimidazolium ethylsulfate, tributylmethyl ammoniumchloride, and combinations thereof.

In one or more embodiments, the one or more direct dye(s) used topre-dye the hair is selected from HC Blue 15, Basic Red 51,hydroxyanthraquinoneaminopropyl methyl morpholinium methosulfate, andcombinations thereof.

In an embodiment, the methods of the present disclosure are utilized tocontrol the removal of certain direct dyes from hair, such as to controlthe speed of removal of certain direct dyes and/or to control the amountof certain direct dyes that are to be removed from hair.

Thus, in an embodiment, the present disclosure pertains to a method ofcontrolling the removal of one or more direct dye(s) from hair, themethod comprising:

a. contacting the hair with a composition comprising:

-   -   i. an organic salt selected from:

an imidazolium-based compound having a structure represented by Formula(I) below:

-   -   wherein R1 and R2 are each independently a linear or branched        alkyl group having 1-16 carbon atoms, and X⁻ is selected from        halides, carboxylates, C₁₋₁₆ fatty acid carboxylates,        phosphates, phosphate derivatives, tosylates, tosylate        derivatives, sulfates or sulfate derivatives,

an ammonium-based compound having a structure represented by Formula(II) below:

-   -   wherein R1, R2, R3 and R4 are each independently a saturated or        unsaturated, linear, branched or cyclic group with a carbon        chain length of C₁₋₂₀, and optionally substituted by one or more        hydroxyl, amino C₁₋₄ radicals, alkylamino, carboxy, carboxylate,        carbamide, C₁₋₄ alkoxy, —SO₃H, sulfonate or aryl; and X⁻ is        selected from halides, carboxylates, C₁₋₁₆ fatty acid        carboxylates, phosphates, phosphate derivatives, tosylates,        tosylate derivatives, sulfates or sulfate derivatives, and    -   a combination thereof; and

b. rinsing the composition from the hair;

wherein the hair has been pre-dyed with one or more direct dye(s) havinga positive Log P_(ow) value, or a direct dye having a negative LogP_(ow) value, or a direct dye having a neutral Log P_(ow) value, orcombinations thereof.

In an embodiment, the method of controlling the removal of one or moredirect dyes from hair includes the method of accelerating the removal ofsaid direct dyes from hair.

In some embodiments, the organic salt is selected frombutyl-3-methylimidazolium octyl sulfate, butyl-3-methylimidazoliumacetate, ethyl-3-methylimidazolium ethylsulfate, tributylmethyl ammoniumchloride, and combinations thereof. In one or more embodiments, the oneor more direct dye(s) used to pre-dye the hair is selected from HC Blue15, Basic Red 51, hydroxyanthraquinoneaminopropyl methyl morpholiniummethosulfate, and combinations thereof.

Another aspect of the disclosure pertains to a method of removing ahydrophobic direct dye from hair, the method comprising:

-   -   a. contacting the hair with a composition comprising:    -   i. an organic salt selected from:        -   1. an imidazolium-based compound having a structure            represented by Formula (I) below:

-   -   wherein:    -   R1 and R2 are each independently a linear or branched alkyl        groups having 1-16 carbon atoms, and X− is selected from        halides, carboxylates, C₁₋₁₆ fatty acid carboxylates, phosphate,        phosphate derivatives, tosylate, tosylate derivatives, sulfate        and sulfate derivatives;        -   2. an ammonium-based compound having a structure represented            by Formula (II) below:

-   -   wherein R1, R2, R3 and R4 are each independently selected from        linear and branched alkyl groups with the carbon chain length of        C₁₋₂₀; and X− is selected from halides, carboxylates, C₁₋₁₆        fatty acid carboxylates, phosphate, phosphate derivatives,        tosylate, tosylate derivatives, sulfate and sulfate derivatives;        and    -   3. a combination thereof; and    -   b. rinsing the composition from hair.

Another aspect of the disclosure pertains to a method of removing acationic direct dye from hair, the method comprising:

a. contacting the hair with a composition comprising:

i. an organic salt selected from:

-   -   1. an imidazolium-based compound having a structure represented        by Formula (I) below:

wherein R1 and R2 are each independently a linear or branched alkylgroups having 1-16 carbon atoms, and X− is selected from halides,carboxylates, C₁₋₁₆ fatty acid carboxylates, phosphate, phosphatederivatives, tosylate, tosylate derivatives, sulfate and sulfatederivatives;

-   -   2. an ammonium-based compound having a structure represented by        Formula (II) below:

-   -   wherein R1, R2, R3 and R4 are each independently selected from        linear and branched alkyl groups with the carbon chain length of        C₁₋₂₀; and X− is selected from halides, carboxylates, C₁₋₁₆        fatty acid carboxylates, phosphate, phosphate derivatives,        tosylate, tosylate derivatives, sulfate and sulfate derivatives;        or

3. a combination thereof; and

b. rinsing the composition from hair.

In an embodiment, the imidazolium-based compound and/or ammonium-basedcompound is present at a concentration of greater than 1 wt. % orranging from greater than 1 to about 50 wt. %, or from about 1 to about30 wt. %, or from about 2 to about 25 wt. %, or from about 3 to about 20wt. %, or from about 3 to about 15 wt. %, or from about 3 to about 10wt. %, based on the total weight of the composition.

In an embodiment, the organic salt comprises an imidazolium-basedcompound selected from the group consisting of butyl-3-methylimidazoliumoctyl sulfate, butyl-3-methylimidazolium acetate,ethyl-3-methylimidazolium ethylsulfate, tributylmethyl ammoniumchloride, and combinations thereof.

In some embodiments, the one or more direct dye(s) comprises a directdye selected from HC Blue 15, hydroxyanthraquinoneaminopropyl methylmorpholinium methosulfate, Basic Red 51, and combinations thereof.

Another aspect of the present disclosure pertains to a method ofremoving the color from or accelerating the removal of color from orlightening the color of hair, the method comprising:

a. contacting the hair with a composition comprising:

i. an organic salt selected from:

-   -   1. an imidazolium-based compound selected from        butyl-3-methylimidazolium octyl sulfate,        butyl-3-methylimidazolium acetate, ethyl-3-methylimidazolium        ethylsulfate, 1-ethyl-3-ethyl imidazolium acetate,        1-ethyl-3-methylimidazolium tosylate, and combinations thereof,        and preferably selected from butyl-3-methylimidazolium octyl        sulfate;    -   2. an ammonium-based compound comprising tributylmethyl ammonium        salt(s); and    -   3. a combination thereof; and        b. rinsing the composition from hair;        wherein the imidazolium-based compound or ammonium-based        compound is present at a concentration ranging from greater than        1 to about 50 wt. %, preferably from about 5 to about 30 wt. %,        based on the total weight of the composition; and        wherein the hair has been pre-dyed with one or more direct        dye(s) selected from hydrophobic direct dyes, cationic direct        dyes, nonionic direct dyes, and combinations thereof.

In an embodiment, the hydrophobic direct dye is selected from HC blue15, hydroxyanthraquinoneaminopropyl methyl morpholinium methosulfate,and combinations thereof.

In an embodiment, the cationic direct dye is selected from basic red 51.

In an embodiment, an amount of the one or more direct dye(s) selectedfrom hydrophobic direct dyes is removed from the hair, thereby resultingin color removal or lightening of the color of the hair.

In an embodiment, an amount of the one or more direct dye(s) selectedfrom cationic direct dyes is removed from the hair, thereby resulting incolor removal or lightening of the color of the hair.

In one embodiment, the method of the present disclosure involvesremoving HC blue 15 and/or hydroxyanthraquinoneaminopropyl methylmorpholinium methosulfate and and/or basic red 51 from hair, the methodcomprising:

-   a. applying onto the hair or contacting the hair with a composition    containing an organic salt selected from an imidazolium-based    compound including butyl-3-methylimidazolium octyl sulfate,    butyl-3-methylimidazolium acetate, ethyl-3-methylimidazolium    ethylsulfate, 1-ethyl-3-ethyl imidazolium acetate,    1-ethyl-3-methylimidazolium tosylate, and combinations thereof, or    an ammonium-based compound including tributylmethyl ammonium    chloride, or combinations thereof; and-   b. rinsing the composition from the hair.

In various embodiments, the method of the present disclosure includes astep of leaving the compositions for removing direct dyes on the hairfor a period of time ranging from about 5 to about 60 minutes.

In various embodiments, the treated hair is heated at a temperatureranging from about 25° C. to about 60° C.

In various embodiments, the compositions of the present disclosure canbe in the form of a spray, gel, cream, lotion, serum, aqueous solution.

In various embodiments, the compositions of the present disclosure canbe a shampoo, rinse-off conditioner, or a rinse-off mask treatment.

In an embodiment, the present disclosure pertains to a hair treatmentagent for removing or controlling the removal of one or more directdye(s) from hair, wherein the agent comprises:

-   -   i. a first composition containing an organic salt selected from:    -   an imidazolium-based compound having a structure represented by        Formula (I) below:

-   -   -   wherein R1 and R2 are each independently a linear or            branched alkyl group having 16 carbon atoms, and X⁻ is            selected from halides, carboxylates, C₁₋₁₆ fatty acid            carboxylates, phosphates, phosphate derivatives, tosylates,            tosylate derivatives, sulfates or sulfate derivatives,

    -   an ammonium-based compound having a structure represented by        Formula (II) below:

-   -   -   wherein R1, R2, R3 and R4 are each independently a saturated            or unsaturated, linear, branched or cyclic group with a            carbon chain length of C₁₋₂₀, and optionally substituted by            one or more hydroxyl, amino C₁₋₄ radicals, alkylamino,            carboxy, carboxylate, carbamide, C₁₋₄ alkoxy, —SO₃H,            sulfonate or aryl; and X⁻ is selected from halides,            carboxylates, C₁₋₁₆ fatty acid carboxylates, phosphates,            phosphate derivatives, tosylates, tosylate derivatives,            sulfates or sulfate derivatives, or

    -   a combination thereof; and

    -   ii. a second composition containing a surfactant selected from        anionic surfactants, amphoteric surfactants, nonionic        surfactants, and combinations thereof;        wherein the first and second compositions are combined to form        the hair treatment agent or the first and second compositions        are applied in a sequential manner or a layering manner onto        hair in any order.

In an embodiment, the present disclosure pertains to a kit containingthe above described first and second compositions in separatecomponents.

In an embodiment, the second composition is a shampoo.

In an embodiment, the composition for removing color or for lighteningthe color of hair pre-dyed with one or more direct dye(s) in accordancewith the present disclosure comprises an organic salt selected from:

an imidazolium-based compound having a structure represented by Formula(I) below:

-   -   wherein R1 and R2 are each independently a linear or branched        alkyl group having 16 carbon atoms, and X⁻ is selected from        halides, carboxylates, C₁₋₁₆ fatty acid carboxylates,        phosphates, phosphate derivatives, tosylates, tosylate        derivatives, sulfates or sulfate derivatives,

an ammonium-based compound having a structure represented by Formula(II) below:

-   -   wherein R1, R2, R3 and R4 are each independently a saturated or        unsaturated, linear, branched or cyclic group with a carbon        chain length of C₁₋₂₀, and optionally substituted by one or more        hydroxyl, amino C₁₋₄ radicals, alkylamino, carboxy, carboxylate,        carbamide, C₁₋₄ alkoxy, —SO₃H, sulfonate or aryl; and X⁻ is        selected from halides, carboxylates, C₁₋₁₆ fatty acid        carboxylates, phosphates, phosphate derivatives, tosylates,        tosylate derivatives, sulfates or sulfate derivatives, and

a combination thereof;

wherein the imidazolium-based compound and/or the ammonium-basedcompound is in ionic liquid form.

As used herein, the term “pre-dyed with one or more direct dye(s)” meansthe hair has been dyed with one or more direct dye(s) prior to contactwith the organic salt or composition containing the organic salt.

As used herein, the term “ionic liquid” refers to the organic salt ofthe present disclosure being in the liquid state or having a meltingpoint of equal to or under 150° C. (preferably 100° C. or preferablyless than 100° C.), or in some embodiments, at room temperature.Preferably, the salt remains liquid up to 300 degrees centigrade, andmore preferably the salt is liquid at room temperature, that is to say,at a melting point of less than or equal to 50 degrees centigrade andgreater than 0 degrees centigrade.

The melting point is measured by differential calorimetric analysis,with a temperature increase rate of 10 degrees centigrade/minute, themelting point then being at a temperature corresponding to the top ofthe endothermic melting peak obtained during the measurement.

According to the disclosure, the term “hydrophobic ionic liquid” meansan ionic liquid having a solubility in water at room temperature (25degrees centigrade) of less than 5 percent, preferably less than 1percent by weight, or even less than 0.5 percent. Within the context ofthe disclosure, the hydrophobic character of the ionic liquid is suchthat there is phase separation in water.

Within the context of the disclosure, the term “water-soluble” means anorganic salt or an ionic liquid which has a solubility in water at 25degrees centigrade of greater than 1 percent, preferably greater than 5percent, more preferably greater than 10 percent; that is to say, whichforms at this concentration a macroscopically homogeneous, transparentand isotropic medium.

As used herein, the term “contacting” means that the composition comesinto contact with the hair so that the composition is exposed to thesurfaces of the hair which would normally accommodate direct dyemolecules or is exposed to the direct dye molecules on the hair. It canalso mean that the composition is applied onto the hair. In someembodiments, this means the hair can be soaked in the compositioncomprising organic salt, or the composition is applied onto the hair byusing the hands or an applicator, or the hair may be mechanicallymanipulated with the composition (e.g. using hands to manipulate hair inthe presence of the composition containing organic salt).

As used herein, the term “rinsing the hair” or “rinsing the compositionfrom the hair” means rinsing or washing the hair with water, orshampooing the hair first, then rinsing the hair with water.

It has been surprisingly discovered that such organic salts are able togreatly accelerate and/or control the removal of direct dyes fromcolor-treated hair. While not wishing to be bound to any particulartheory, it is believed that the organic salts are able to physicallyextract the direct dyes which reside on the surface of hair fibers, assuch dye molecules interact with hair protein by non-covalent bonds. Itis also believed that the physical extraction of the dyes presents amild approach to treating hair or removing dyes from dyed hair withoutintroducing harsh chemicals or chemical reactions on hair that candamage or negatively impact the integrity or quality of hair fibers. Itis also thought that the organic salts have a high swelling ability inhair fibers.

It has further been discovered that this acceleration can be furtherenhanced by also including a surfactant in the process, particularly fordyes which have a positive Log P_(ow) value and/or are hydrophobic.While not wishing to be bound by any particular theory, it is thoughtthe surfactants and organic salts form binary surfactant systems andfurther enhance color removal by increasing both hair wettability anddye solubility, and interact with the dyes by ionic or hydrophobicinteraction.

Compositions

Organic Salt

The compositions comprise at least one organic salt. The organic salt ofthe present disclosure can comprise an organic cation and an inorganicanionic or an inorganic cation and an organic anion or an organic cationand an organic anion.

In an embodiment, the organic salt of the present disclosure comprisesan imidazolium-based compound.

In an embodiment, the organic salt of the present disclosure comprisesan ammonium-based compound.

In an embodiment, the organic salt of the present disclosure comprisesan imidazolium-based compound and an ammonium-based compound.

Imidazolium-Based Compounds

According to one or more embodiments, the organic salt comprises animidazolium-based compound having a structure represented by Formula (I)below:

-   -   wherein R1 and R2 are each independently selected from linear        and branched alkyl groups having 1-16 carbon atoms, and X⁻ is        selected from halides, carboxylates, C₁₋₁₆ fatty acid        carboxylates, phosphate, phosphate derivatives, tosylate,        tosylate derivatives, sulfate and sulfate derivatives.

In one or more embodiments, each R group is each independently selectedfrom methyl, ethyl, propyl or butyl. In some embodiments, R2 is methyl,ethyl, propyl, or butyl and R1 is methyl, ethyl, propyl, or butyl, inany combination. Examples include butyl-3-methylimidazolium,butyl-3-methylimidazolium, ethyl-3-methylimidazolium, 1,3-ethylimidazolium.

In some embodiments, X⁻ comprises a halide. In further embodiments, thehalide comprises F⁻, Br⁻, Cl⁻, or I⁻. In one or more embodiments, X⁻comprises a phosphate, phosphate derivatives, tosylate, tosylatederivatives, sulfate and sulfate derivatives. Such phosphate, tosylateand sulfate derivatives may include alkyl phosphates, alkyl tosylatesand alkyl sulfates, respectively. Such phosphate, tosylate and sulfatederivatives may also include halo phosphates, halo tosylates and halosulfates, respectively. The alkyl groups of such alkyl sulfates couldinclude 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms. In furtherembodiments, the alkyl sulfate comprises ethyl sulfate or octyl sulfate.In some embodiments, X⁻ comprises a carboxylate or fatty acidcarboxylate. The fatty acid carboxylate could include 1, 2, 3, 4, 5, 6,7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms. In further embodiments, thecarboxylate comprises acetate.

In some embodiments, the organic salt comprises an imidazolium-basedcompound selected from the group consisting of butyl-3-methylimidazoliumoctyl sulfate, butyl-3-methylimidazolium acetate,ethyl-3-methylimidazolium ethylsulfate, 1,3-ethyl imidazolium acetate,and combinations thereof.

Ammonium-Based Compounds

According to one or more embodiments, the organic salt comprises anammonium-based compound having a structure represented by Formula (II)below:

-   -   wherein R1, R2, R3 and R4 are each independently selected from        saturated or unsaturated, linear, branched or cyclic groups with        the carbon chain length of C₁₋₂₀, which are optionally        substituted by one or more hydroxyl, amino C₁₋₄ radicals,        alkylamino, carboxy, carboxylate, carbamide, C₁₋₄ alkoxy, —SO₃H,        sulfonate or aryl; and X⁻ is selected from the group consisting        of halides, carboxylates, C₁₋₁₆ fatty acid carboxylates,        phosphate, phosphate derivatives, tosylate, tosylate        derivatives, sulfate and sulfate derivatives.

In some embodiments, R1, R2, R3 and R4 are each independently selectedfrom linear and branched alkyl groups with the carbon chain length ofC₁₋₂₀.

In one or more embodiments, R1 is methyl, ethyl, propyl, butyl, pentyl,hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, trydecyl,tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl oreicosyl; R2 is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl,octyl, nonyl, decyl, undecyl, dodecyl, trydecyl, tetradecyl, pentadecyl,hexadecyl, heptadecyl, octadecyl, nonadecyl or eicosyl; R3 is methyl,ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl,undecyl, dodecyl, trydecyl, tetradecyl, pentadecyl, hexadecyl,heptadecyl, octadecyl, nonadecyl or eicosyl; and R4 is methyl, ethyl,propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl,dodecyl, trydecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl,octadecyl, nonadecyl or eicosyl in any combination.

In one or more embodiments, the ammonium-based compound has a structureselected from the group consisting of:

In some embodiments, X⁻ comprises a halide. In further embodiments, thehalide comprises F⁻, Br⁻, Cl⁻, or I⁻. In one or more embodiments, X⁻comprises a phosphate, phosphate derivatives, tosylate, tosylatederivatives, sulfate and sulfate derivatives. Such phosphate, tosylateand sulfate derivatives may include alkyl phosphates, alkyl tosylatesand alkyl sulfates, respectively. Such phosphate, tosylate and sulfatederivatives may also include halo phosphates, halo tosylates and halosulfates, respectively. The alkyl groups of such alkyl sulfates couldinclude 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16 carbonatoms. In further embodiments, the alkyl sulfate comprises ethyl sulfateor octyl sulfate. In some embodiments, X⁻ comprises a carboxylate orfatty acid carboxylate. The fatty acid carboxylate could include 1, 2,3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms. In furtherembodiments, the carboxylate comprises acetate.

In some embodiments, the organic salt in the present disclosurecomprises an ammonium-based compound including tributylmethyl ammoniumchloride (TBuMA Cl).

The organic salt (or salt of an organic molecule) of the presentdisclosure can be in the form of an ionic liquid. In some embodiments,the ionic liquid can hydrophobic. In some other embodiments, the ionicliquid can be water-soluble.

In one or more embodiments, the organic salt includes animidazolium-based compound in ionic liquid form.

In one or more embodiments, the organic salt includes an ammonium-basedcompound in ionic liquid form.

In one or more embodiments, the organic salt includes animidazolium-based compound and ammonium-based compound in ionic liquidforms.

In one or more embodiments, the organic salt includes animidazolium-based compound in ionic liquid form and selected frombutyl-3-methylimidazolium octyl sulfate, butyl-3-methylimidazoliumacetate, ethyl-3-methylimidazolium ethylsulfate, tributylmethyl ammoniumchloride, and combinations thereof.

In one or more embodiments, the organic salt comprises animidazolium-based compound and/or an ammonium-based compound that arenot in ionic liquid form or that are in ionic liquid form or that arecombinations of salts that are not in ionic liquid form and salts thatare in ionic liquid form.

In one or more embodiments, the organic salt is contained in or combinedwith a solvent such as water or one or more organic solvents or amixture of water and one or more organic solvents.

In an embodiment, when the organic salt is contained in or combined witha solvent such as water or one or more organic solvents or a mixture ofwater and one or more organic solvents, the organic salt dissociatesinto cations and anions in the solvent (i.e., the organic salt is nolonger in ionic liquid form).

In an embodiment, when the organic salt comprises an ionic liquid and iscontained in or combined with a solvent such as water or one or moreorganic solvents or a mixture of water and one or more organic solvents,a portion of the organic salt dissociates into cations and anions in thesolvent (i.e., the organic salt is no longer in ionic liquid form) and aportion of the organic salt remains an ionic liquid.

In one or more embodiments, the organic salts in the methods andcompositions of the present disclosure are advantageously used on hairthat has been dyed with direct dyes, in particular, hydrophobic dyesand/or dyes which have a positive Log P_(ow) value, in order toaccelerate color removal. Such hydrophobic dyes interact with hairfibers through strong hydrophobic interactions, and are thus difficultto be removed using general washing with water or shampooing withconventional shampoos. In some embodiments, the dyes advantageouslyremoved using organic salts contain an anthraquinone derivative and/ormulti-aromatic rings, and have low solubility in water.

In various embodiments, the organic salt may be present in thecomposition at a concentration ranging from about 0.01, 0.1, 0.2, 0.3,0.4, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 19,20, 25, 30, 35 or 40 to about 15, 16, 17, 19, 20, 25, 30, 35, 40, 45,50, 55, 60, 65 or 70 wt. % by total weight of the composition. In someembodiments, the organic salt may be present at a concentration rangingfrom about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17,19, 20, 25, 30, 35 or 40 to about 15, 16, 17, 19, 20, 25, 30, 35, 40,45, 50, 55, 60, 65 or 70 wt. % by total weight of the composition. Inembodiments when a surfactant is present, the organic salt may bepresent at a concentration ranging from about 0.01, 0.1, 0.2, 0.3, 0.4,0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 19, 20,25, 30, 35 or 40 to about 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17,19, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65 or 70 wt. % by total weightof the composition.

In other embodiments, the total amount of the organic salt in thecomposition of the present disclosure is greater than 1 wt %, based onthe total weight of the composition. In some cases, the total amount ofthe organic salt in the composition ranges from greater than 1 to about50 wt. %, or from about 2 to about 40 wt. %, or from about 4 to about 35wt. %, or from about 5 to about 30 wt. %, or from about 5 to about 25wt. %, or from about 5 to about 20 wt. %, or from about 5 to about 15wt. %, or from about 5 to about 10 wt. %, or from about 10 to about 50wt. %, or from about 20 to about 50 wt. %, or from about 25 to about 50wt. %, based on the total weight of the composition, including rangesand sub-ranges therebetween.

For example, when the organic salt is selected frombutyl-3-methylimidazolium octyl sulfate, butyl-3-methylimidazoliumacetate, ethyl-3-methylimidazolium ethylsulfate, 1-ethyl-3-ethylimidazolium acetate, 1-ethyl-3-methylimidazolium tosylate,tributylmethyl ammonium chloride, and combinations thereof, the totalamount of the organic salt in the composition may range from greaterthan 1 to about 50 wt. %, or from about 2 to about 40 wt. %, or fromabout 4 to about 35 wt. %, or from about 5 to about 30 wt. %, or fromabout 5 to about 25 wt. %, or from about 5 to about 20 wt. %, or fromabout 5 to about 15 wt. %, or from about 5 to about 10 wt. %, based onthe total weight of the composition, including ranges and sub-rangestherebetween.

As a further example, when the organic salt is selected frombutyl-3-methylimidazolium octyl sulfate, butyl-3-methylimidazoliumacetate, ethyl-3-methylimidazolium ethylsulfate, 1-ethyl-3-ethylimidazolium acetate, 1-ethyl-3-methylimidazolium tosylate,tributylmethyl ammonium chloride, and combinations thereof, the totalamount of the organic salt in the composition may be about 2, 3, 4, 5,6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 wt. %, basedon the total weight of the composition.

Surfactants

Although not required, in some embodiments surfactants or emulsifiersare used in combination with the organic salts of the present disclosurein order to further accelerate the removal of color from or lighten thecolor of hair dyed with direct dyes (semi-permanent color). If thesurfactant has a very long hydrocarbon chain (i.e., more than 18-20carbons), other emulsifiers may advantageously be added. In someembodiments, the direct dye used to color hair has a positive Log P_(ow)value and the compositions containing organic salts according to thedisclosure preferentially comprise at least one surfactant.

Anionic Surfactant

The term “anionic surfactant” means a surfactant comprising, as ionic orionizable groups, only anionic groups. A species is termed as being“anionic” when it bears at least one permanent negative charge or whenit can be ionized as a negatively charged species, under the conditionsof use of the composition (for example the medium or the pH) and notcomprising any cationic charge. These anionic groups may be chosen from—CO₂H, —CO₂ ⁻, —SO₃H, —SO₃ ⁻, —OSO₃H, —OSO₃ ⁻, —H₂PO₃, —HPO₃ ⁻, —PO₃ ²⁻,—H₂PO₂, ═HPO₂, —HPO₂ ⁻, ═PO₂ ⁻, ═POH, and ═PO⁻ groups.

The anionic surfactants may be sulfate, sulfonate and/or carboxylic (orcarboxylate) surfactants, or mixtures thereof.

Sulfate anionic surfactants comprise at least one sulfate function butdo not comprise any carboxylate or sulfonate functions. The sulfateanionic surfactants that may be used comprise at least one sulfatefunction (—OSO₃H or —OSO₃).

They may be chosen from the following compounds: alkyl sulfates, alkylether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates,monoglyceride sulfates; and also the salts of these compounds; the alkylgroups of these compounds comprising from 6 to 30 carbon atoms,especially from 12 to 28, better still from 14 to 24 or even from 16 to22 carbon atoms; the aryl group preferably denoting a phenyl or benzylgroup; these compounds possibly being polyoxyalkylenated, especiallypolyoxyethylenated, and then preferably comprising from 1 to 50 ethyleneoxide units and better still from 2 to 10 ethylene oxide units.

Preferentially, the sulfate anionic surfactants are chosen, alone or asa mixture, from:

-   -   alkyl sulfates, especially of C6-C24 or even C12-C20,    -   alkyl ether sulfates, especially of C6-C24 or even C12-C20,        preferably comprising from 2 to 20 ethylene oxide units;    -   in particular in the form of alkali metal or alkaline-earth        metal, ammonium or amino alcohol salts.

Sulfonate anionic surfactants comprise at least one sulfonate function(—SO₃H or —SO₃ ⁻) and may optionally also comprise one or more sulfatefunctions, but do not comprise any carboxylate functions. The sulfonateanionic surfactants that may be used comprise at least one sulfonatefunction (—SO₃H or —SO₃—).

They may be chosen from the following compounds: alkylsulfonates,alkylamidesulfonates, alkylarylsulfonates, α-olefinsulfonates, paraffinsulfonates, alkylsulfosuccinates, alkyl ether sulfosuccinates,alkylamidesulfosuccinates, alkylsulfoacetates, N-acyltaurates,acylisethionates; alkylsulfolaurates; and also the salts of thesecompounds; the alkyl groups of these compounds comprising from 6 to 30carbon atoms, especially from 12 to 28, better still from 14 to 24 oreven from 16 to 22 carbon atoms; the aryl group preferably denoting aphenyl or benzyl group; these compounds possibly beingpolyoxyalkylenated, especially polyoxyethylenated, and then preferablycomprising from 1 to 50 ethylene oxide units and better still from 2 to10 ethylene oxide units.

Preferentially, the sulfonate anionic surfactants are chosen, alone oras a mixture, from:

-   -   C6-C24 and especially C12-C20 alkylsulfosuccinates, especially        laurylsulfosuccinates;    -   C6-C24 and especially C12-C20 alkyl ether sulfosuccinates; and    -   (C6-C24)acylisethionates and preferably        (C12-C18)acylisethionates,        in particular in the form of alkali metal or alkaline-earth        metal, ammonium or amino alcohol salts.

Carboxylate anionic surfactants comprise at least one carboxylic orcarboxylate function (—COOH or —COO⁻) and may optionally also compriseone or more sulfate and/or sulfonate functions. The carboxylic anionicsurfactants that may be used thus comprise at least one carboxylic orcarboxylate function (—COOH or —COO⁻).

They may be chosen from the following compounds: acylglycinates,acyllactylates, acylsarcosinates, acylglutamates;alkyl-D-galactosideuronic acids, alkyl ether carboxylic acids,alkyl(C6-30 aryl) ether carboxylic acids, alkylamido ether carboxylicacids; and also the salts of these compounds; the alkyl and/or acylgroups of these compounds comprising from 6 to 30 carbon atoms,especially from 12 to 28, better still from 14 to 24 or even from 16 to22 carbon atoms; the aryl group preferably denoting a phenyl or benzylgroup; these compounds possibly being polyoxyalkylenated, especiallypolyoxyethylenated, and then preferably comprising from 1 to 50 ethyleneoxide units and better still from 2 to 10 ethylene oxide units.

Use may also be made of the C6-C24 alkyl monoesters ofpolyglycoside-polycarboxylic acids, such as C6-C24 alkylpolyglycoside-citrates, C6-C24 alkyl polyglycoside-tartrates and C6-C24alkyl polyglycoside-sulfosuccinates, and salts thereof.

Among the above carboxylic surfactants, mention may be made mostparticularly of polyoxyalkylenated alkyl(amido) ether carboxylic acidsand salts thereof, in particular those comprising from 2 to 50 alkyleneoxide and in particular ethylene oxide groups, such as the compoundssold by the company Kao under the name Akypo.

The polyoxyalkylenated alkyl(amido) ether carboxylic acids that may beused are preferably chosen from those of formula (1):R₁—(OC₂H₄)_(n)—OCH₂COOA  (1)

-   -   wherein:        -   R¹ represents a linear or branched C6-C24 alkyl or alkenyl            radical, an alkyl(C8-C9)phenyl radical, a radical            R2CONH—CH2-CH2- with R2 denoting a linear or branched C9-C21            alkyl or alkenyl radical, preferably, R1 is a C8-C20 and            preferably C8-C18 alkyl radical, and aryl preferably denotes            phenyl,        -   n is an integer or decimal number (average value) ranging            from 2 to 24 and preferably from 2 to 10,        -   A denotes H, ammonium, Na, K, Li, Mg or a monoethanolamine            or triethanolamine residue.

It is also possible to use mixtures of compounds of formula (1), inparticular mixtures of compounds containing different groups R1.

The polyoxyalkylenated alkyl(amido) ether carboxylic acids that areparticularly preferred are those of formula (1) in which:

-   -   R1 denotes a C12-C14 alkyl, cocoyl, oleyl, nonylphenyl or        octylphenyl radical,    -   A denotes a hydrogen or sodium atom, and    -   n varies from 2 to 20 and preferably from 2 to 10.

Even more preferentially, use is made of compounds of formula (1) inwhich R denotes a C12 alkyl radical, A denotes a hydrogen or sodium atomand n ranges from 2 to 10.

Preferentially, the carboxylic anionic surfactants are chosen, alone oras a mixture, from:

-   -   acylglutamates, especially of C6-C24 or even C12-C20, such as        stearoylglutamates, and in particular disodium        stearoylglutamate;    -   acylsarcosinates, especially of C6-C24 or even C12-C20, such as        palmitoylsarcosinates, and in particular sodium        palmitoylsarcosinate;    -   acyllactylates, especially of C12-C28 or even C14-C24, such as        behenoyllactylates, and in particular sodium behenoyllactylate;    -   C6-C24 and especially C12-C20 acylglycinates;    -   (C6-C24)alkyl ether carboxylates and especially (C12-C20)alkyl        ether carboxylates;    -   polyoxyalkylenated (C₆-C₂₄)alkyl(amido) ether carboxylic acids,        in particular those comprising from 2 to 50 ethylene oxide        groups; in particular in the form of alkali metal or        alkaline-earth metal, ammonium or amino alcohol salts.

When the anionic surfactant is in salt form, the said salt may be chosenfrom alkali metal salts, such as the sodium or potassium salt, ammoniumsalts, amine salts and in particular amino alcohol salts, andalkaline-earth metal salts, such as the magnesium salt.

Examples of amino alcohol salts that may be mentioned includemonoethanolamine, diethanolamine and triethanolamine salts,monoisopropanolamine, diisopropanolamine or triisopropanolamine salts,2-amino-2-methyl-1-propanol salts, 2-amino-2-methyl-1,3-propanediolsalts and tris(hydroxymethyl)aminomethane salts.

Alkali metal or alkaline-earth metal salts and in particular the sodiumor magnesium salts are preferably used.

Preferentially, the anionic surfactants are chosen, alone or as amixture, from:

-   -   C6-C24 and especially C12-C20 alkyl sulfates;    -   C6-C24 and especially C12-C20 alkyl ether sulfates; preferably        comprising from 2 to 20 ethylene oxide units;    -   C6-C24 and especially C12-C20 alkylsulfosuccinates, especially        laurylsulfosuccinates;    -   C6-C24 and especially C12-C20 alkyl ether sulfosuccinates;    -   (C6-C24)acylisethionates and preferably        (C12-C18)acylisethionates;    -   C6-C24 and especially C12-C20 acylsarcosinates; especially        palmitoylsarcosinates;    -   (C6-C24)alkyl ether carboxylates, preferably (C12-C20)alkyl        ether carboxylates;    -   polyoxyalkylenated (C6-C24)alkyl(amido) ether carboxylic acids        and salts thereof, in particular those comprising from 2 to 50        alkylene oxide and in particular ethylene oxide groups;    -   C6-C24 and especially C12-C20 acylglutamates;    -   C6-C24 and especially C12-C20 acylglycinates;    -   in particular in the form of alkali metal or alkaline-earth        metal, ammonium or amino alcohol salts.

In particular, (C₁₂-C₂₀)alkyl sulfates, (C₁₂-C₂₀)alkyl ether sulfatescomprising from 2 to 20 ethylene oxide units, especially in the form ofalkali metal, ammonium, amino alcohol and alkaline-earth metal salts, ora mixture of these compounds, may be chosen. In at least one embodiment,sodium lauryl ether sulfate containing 2.2 mol of ethylene oxide ischosen.

In other embodiments, the anionic surfactant is chosen from sodiumlaureth sulfate, sodium lauryl sulfate, sodium lauroyl methylisethionate, and mixtures thereof.

Amphoteric or Zwitterionic Surfactant

In one or more embodiments, the surfactant comprises one or moreamphoteric surfactants. The amphoteric surfactants that may be used incompositions according to the disclosure may be optionally quaternizedsecondary or tertiary aliphatic amine derivatives, in which thealiphatic group is a linear or branched chain comprising from 8 to 22carbon atoms, said amine derivatives containing at least one anionicgroup, for instance a carboxylate, sulfonate, sulfate, phosphate orphosphonate group. Mention may be made in particular of(C8-C20)alkylbetaines, sulfobetaines, (C8-C20)alkylsulfobetaines,(C8-C20)alkylamido(C1-C6)alkylbetaines, such as cocamidopropylbetaine,and (C8-C20)alkylamido(C1-C6)alkylsulfobetaines, and mixtures thereof.Among the optionally quaternized secondary or tertiary aliphatic aminederivatives that may be used, mention may also be made of the productsof respective structures (A1) and (A2) below:R_(a)—CON(Z)CH₂—(CH₂)_(m)—N⁺(R_(b))(R_(c))(CH₂COO⁻)  (A1)

wherein:

-   -   R_(a) represents a C₁₀-C₃₀ alkyl or alkenyl group derived from        an acid R_(a)—COOH preferably present in hydrolysed coconut oil,        a heptyl group, a nonyl group or an undecyl group,    -   R_(b) represents a β-hydroxyethyl group,    -   R_(c) represents a carboxymethyl group;    -   m is equal to 0, 1 or 2,    -   Z represents a hydrogen atom or a hydroxyethyl or carboxymethyl        group; and        R_(a)—CON(Z)CH₂—(CH₂)_(m)—N(B)(B′)  (A2)

wherein:

-   -   B represents —CH₂CH₂OX′, with X′ representing —CH₂—COOH,        CH₂—COOZ′, —CH₂CH₂—COOH, —CH₂CH₂—COOZ′, or a hydrogen atom,    -   B′ represents —(CH₂)_(z)—Y′, with z=1 or 2, and Y′ representing        —COOH, —COOZ′, —CH₂—CHOH—SO₃H or —CH₂—CHOH—SO₃Z′,    -   m′ is equal to 0, 1 or 2,    -   Z represents a hydrogen atom or a hydroxyethyl or carboxymethyl        group,    -   Z′ represents an ion resulting from an alkali or alkaline-earth        metal, such as sodium, potassium or magnesium; an ammonium ion;        or an ion resulting from an organic amine and in particular from        an amino alcohol, such as monoethanolamine, diethanolamine and        triethanolamine, monoisopropanolamine, diisopropanolamine or        triisopropanolamine, 2-amino-2-methyl-1-propanol,        2-amino-2-methyl-1,3-propanediol and        tris(hydroxymethyl)aminomethane,    -   R_(a′) represents a C₁₀-C₃₀ alkyl or alkenyl group of an acid        R_(a′)COOH preferably present in hydrolysed linseed oil or        coconut oil, an alkyl group, in particular a C₁₇ alkyl group,        and its iso form, or an unsaturated C₁₇ group.

Among the compounds corresponding to formula (A2) in which X′ representsa hydrogen atom, mention may be made of compounds classified in the CTFAdictionary, under the names sodium cocoamphoacetate, sodiumlauroamphoacetate, sodium caproamphoacetate and sodiumcapryloamphoacetate.

Other compounds corresponding to formula (A2) are disodiumcocoamphodiacetate, disodium lauroamphodiacetate, disodiumcaproamphodiacetate, disodium capryloamphodiacetate, disodiumcocoamphodipropionate, disodium lauroamphodipropionate, disodiumcaproamphodipropionate, disodium capryloamphodipropionate,lauroamphodipropionic acid and cocoamphodipropionic acid.

Examples that may be mentioned include the cocoamphodiacetate sold bythe company Rhodia under the trade name Miranol® C2M Concentrate, thesodium cocoamphoacetate sold under the trade name Miranol Ultra C 32 andthe product sold by the company Chimex under the trade name CHIMEXANEHA.

Use may also be made of the compounds of formula (A3):R_(a′)NH—CH(Y″)—(CH₂)n-C(O)—NH—(CH₂)n′—N(R_(d))(R_(e))  (A3)

wherein:

-   -   R_(a″) represents a C₁₀-C₃₀ alkyl or alkenyl group of an acid        R_(a′)—C(O)OH preferably present in hydrolysed linseed oil or        coconut oil;    -   Y″ represents the group —C(O)OH, —C(O)OZ″, —CH₂—CH(OH)—SO₃H or        the group —CH₂—CH(OH)—SO₃—Z″, with Z″ representing a cationic        counterion resulting from an alkali metal or alkaline-earth        metal, such as sodium, an ammonium ion or an ion resulting from        an organic amine;    -   R_(d) and R_(e) represent, independently of each other, a C1-C4        alkyl or hydroxyalkyl radical; and    -   n and n′ denote, independently of each other, an integer ranging        from 1 to 3.

Among the compounds corresponding to formula (A3), mention may inparticular be made of the compound classified in the CTFA dictionaryunder the name sodium diethylaminopropyl cocoaspartamide, such as theone sold by the company Chimex under the name CHIMEXANE HB.

Preferably, the amphoteric surfactants are chosen from(C8-C20)alkylbetaines, (C8-C20)alkylamido(C1-C6)alkylbetaines,(C8-C20)alkylamphoacetates and (C8-C20)alkylamphodiacetates, andmixtures thereof.

In preferred embodiments of the disclosure, the amphoteric surfactantsare chosen from coco-betaine sold by BASF as DEHYTON AB 30.

Non-Ionic Surfactant

Examples of nonionic surfactants that may be used in the compositionaccording to embodiments of the disclosure are described, for example,in the Handbook of Surfactants by M. R. Porter, published by Blackie &Son (Glasgow and London), 1991, pp. 116-178. They are especially chosenfrom alcohols, α-diols and (C₁-C₂₀) alkylphenols, these compounds beingpolyethoxylated, polypropoxylated and/or polyglycerolated, the number ofethylene oxide and/or propylene oxide groups possibly ranging from 1 to100, and the number of glycerol groups possibly ranging from 2 to 30; oralternatively these compounds comprising at least one fatty chaincomprising from 8 to 30 carbon atoms and especially from 16 to 30 carbonatoms.

Mention may also be made of alkoxylated alcohols, such as condensates ofethylene oxide and of propylene oxide with fatty alcohols;polyethoxylated fatty amides preferably having from 2 to 30 ethyleneoxide units, polyglycerolated fatty amides comprising on average from 1to 5, and in particular from 1.5 to 4, glycerol groups; ethoxylatedfatty acid esters of sorbitan preferably containing from 2 to 40ethylene oxide units, fatty acid esters of sucrose, polyoxyalkylenatedand preferably polyoxyethylenated fatty acid esters containing from 2 to150 mol of ethylene oxide, including oxyethylenated plant oils, N—(C6-24alkyl)glucamine derivatives, amine oxides such as (C10-14 alkyl)amineoxides or N—(C10-14 acyl)aminopropylmorpholine oxides. Mention may alsobe made of PEG-40 hydrogenated castor oil.

Mention may also be made of nonionic surfactants of alkyl(poly)glycosidetype (also called “alkylpolyglucoside”) represented especially by thefollowing general formula:R₁O—(R₂O)_(t)-(G)_(v)

wherein:

-   -   R₁ represents a linear or branched alkyl or alkenyl radical        comprising 6 to 24 carbon atoms and especially 8 to 18 carbon        atoms, or an alkylphenyl radical whose linear or branched alkyl        radical comprises 6 to 24 carbon atoms and especially 8 to 18        carbon atoms;    -   R2 represents an alkylene radical comprising 2 to 4 carbon        atoms,    -   G represents a sugar unit comprising 5 to 6 carbon atoms,    -   t denotes a value ranging from 0 to 10 and preferably 0 to 4,    -   v denotes a value ranging from 1 to 15 and preferably 1 to 4.

Preferably, the alkylpolyglycoside surfactants are compounds of theformula described above in which:

-   -   R₁ denotes a linear or branched, saturated or unsaturated alkyl        radical comprising from 8 to 18 carbon atoms,    -   R₂ represents an alkylene radical comprising 2 to 4 carbon        atoms,    -   t denotes a value ranging from 0 to 3 and preferably equal to 0,    -   G denotes glucose, fructose or galactose, preferably glucose;    -   the degree of polymerization, i.e. the value of v, possibly        ranging from 1 to 15 and preferably from 1 to 4; the mean degree        of polymerization more particularly being between 1 and 2.

The glucoside bonds between the sugar units are generally of 1-6 or 1-4type and preferably of 1-4 type. Preferably, the alkyl(poly)glycosidesurfactant is an alkyl(poly)glucoside surfactant. C8/C16alkyl(poly)glycosides 1,4, and especially decyl glucosides andcaprylyl/capryl glucosides, are most particularly preferred.

Among the commercial products, mention may be made of the products soldby the company BASF under the names PLANTAREN® (600 CS/U, 1200 and 2000)or PLANTACARE® (818, 1200 and 2000); the products sold by the companySEPPIC under the names ORAMIX CG 110 and ORAMIX NS 10; the products soldby the company BASF under the name LUTENSOL GD 70, or else the productssold by the company CHEM Y under the name AG10 LK.

Preferably, use is made of C8/C16-alkyl(poly)glycosides-1,4, especiallyas an aqueous 53% solution, such as those sold by Cognis under thereference Plantacare® 818 UP.

Other examples of nonionic surfactants that may be used in the presentdisclosure comprise fatty acid alkanolamides (isopropanolamides of fattyacids) such as cocoamide MIPA, lauramide MIPA, Linoleamide MIPA,Myristamide MIPA, Oleamide MIPA, stearamide MIPA, isostearamide MIPA,and mixtures thereof.

Mention may also be made of nonionic surfactants chosen from PEG-40hydrogented castor oil.

In certain embodiments, the nonionic surfactants of the presentdisclosure are chosen from (C6-24 alkyl)polyglycosides, and from fattyacid alkanolamides, and more particularly (C8-18 alkyl)(poly)glycosides,ethoxylated C8-C30 fatty acid esters of sorbitan, polyethoxylated C8-C30fatty alcohols and polyoxyethylenated C8-C30 fatty acid esters, thesecompounds preferably containing from 2 to 150 mol of ethylene oxide, andmixtures thereof.

In preferred embodiments of the disclosure, the nonionic surfactants arechosen from coco-glucoside, cocamide MIPA, PEG-40 hydrogenated castoroil, and mixtures thereof.

In some embodiments, the nonionic surfactant in the composition of thepresent disclosure is coco-glucoside. In other embodiments, the nonionicsurfactant comprises coco-glucoside and cocamide MIPA.

In various embodiments, when present, the surfactant may be used at aconcentration ranging from about 0.01, 0.1, 0.2, 0.3, 0.4, 0.5, 1, 2, 3,4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 19, 20, 25, 30, 35 or40 to about 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16,17, 19, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65 or 70 wt. %, based on thetotal weight of the composition.

Solvents

Compositions according to the disclosure comprise a solvent. The solventmay be chosen from water, organic solvents, or mixtures thereof.

In some embodiments, the solvent comprises, consists essentially of, orconsists of water. The total amount of water in the compositions mayvary depending on the type of composition and the desired consistency,viscosity, etc.

In certain embodiments, the composition comprises, consists essentiallyof, or consists of non-organic solvents, for example, glycerin, C₁₋₄alcohols, fatty alcohols, fatty ethers, fatty esters, polyols, glycols,vegetable oils, mineral oils, liposomes, laminar lipid materials, or anya mixture thereof. Non-limiting examples of solvents which may be usedinclude alkanediols such as glycerin, 1,2,6-hexanetriol,trimethylolpropane, ethylene glycol, propylene glycol, diethyleneglycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol,dipropylene glycol, 2-butene-1,4-diol, 2-ethyl-1,3-hexanediol,2-methyl-2,4-pentanediol, caprylyl glycol, 1,2-hexanediol,1,2-pentanediol, and 4-methyl-1,2-pentanediol; alkyl alcohols having 1to 4 carbon atoms such as ethanol, methanol, butanol, propanol, andisopropanol; glycol ethers such as ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, ethylene glycol monobutyl ether,ethylene glycol monomethyl ether acetate, diethylene glycol monomethylether, diethylene glycol monoethyl ether, diethylene glycolmono-n-propyl ether, ethylene glycol mono-iso-propyl ether, diethyleneglycol mono-iso-propyl ether, ethylene glycol mono-n-butyl ether,ethylene glycol mono-t-butyl ether, diethylene glycol mono-t-butylether, 1-methyl-1-methoxybutanol, propylene glycol monomethyl ether,propylene glycol monoethyl ether, propylene glycol mono-t-butyl ether,propylene glycol mono-n-propyl ether, propylene glycol mono-iso-propylether, dipropylene glycol monomethyl ether, dipropylene glycol monoethylether, dipropylene glycol mono-n-propyl ether, and dipropylene glycolmono-iso-propyl ether; 2-pyrrolidone, N-methyl-2-pyrrolidone,1,3-dimethyl-2-imidazolidinone, formamide, acetamide, dimethylsulfoxide, sorbit, sorbitan, acetine, diacetine, triacetine, sulfolane,or mixtures thereof.

In some cases, the solvent may be selected from the group consisting ofone or more glycols, C₁₋₄ alcohols, glycerin, and a mixture thereof. Forexample, the solvent may be selected from the group consisting ofhexylene glycol, proplene glycol, caprylyl glycol, glycerin, isopropylalcohol, or mixtures thereof.

Polyhydric alcohols are useful. Examples of polyhydric alcohols includeglycerin, ethylene glycol, diethylene glycol, triethylene glycol,propylene glycol, dipropylene glycol, tripropylene glycol,1,3-butanediol, 2,3-butanediol, 1,4-butanediol, 3-methyl-1,3-butanediol,1,5-pentanediol, tetraethylene glycol, 1,6-hexanediol,2-methyl-2,4-pentanediol, polyethylene glycol, 1,2,4-butanetriol,1,2,6-hexanetriol, or mixtures thereof.

Polyol compounds may also be used. Non-limiting examples include thealiphatic diols, such as 2-ethyl-2-methyl-1,3-propanediol,3,3-dimethyl-1,2-butanediol, 2,2-diethyl-1,3-propanediol,2-methyl-2-propyl-1,3-propanediol, 2,4-dimethyl-2,4-pentanediol,2,5-dimethyl-2,5-hexanediol, 5-hexene-1,2-diol, and2-ethyl-1,3-hexanediol, or mixtures thereof.

The solvent may be present in the composition in an amount ranging fromabout 60% to about 98% by weight, relative to the total weight of thecomposition, including all ranges and subranges therebetween. Forexample, in one embodiment, the total amount of water may be about 75%to about 98%, about 75% to about 95%, about 75% to 93%, or about 75% to90% by weight, relative to the total weight of the composition.

Additional Components

The compositions according to the disclosure may also comprise additiveschosen from anionic polymers, nonionic polymers, rheoLogy modifiers,thickening and/or viscosity modifying agents, associative ornon-associative polymeric thickeners, non-polymeric thickeners,non-polymeric cationic surfactants, nacreous agents, dyes or pigments,fragrances, mineral, plant or synthetic oils, waxes, vitamins, proteinsincluding ceramides, vitamins, UV-screening agents, free-radicalscavengers, antidandruff agents, hair-loss counteractants, hairrestorers, preserving agents, pH stabilizers and solvents, and mixturesthereof. A person skilled in the art will take care to select theoptional additives and the amount thereof such that they do not harm theproperties of the compositions of the present disclosure.

If present, these additives are generally present in an amount rangingup to about 40% by weight of active material relative to the totalweight of the composition, such as up to about 30%, up to about 20%, upto about 15%, up to about 10%, up to about 5%, such as from 0% to 20%.

The compositions of certain embodiments may comprise stabilizers, forexample sodium chloride, magnesium dichloride or magnesium sulfate.

The rheoLogy modifiers and thickening/viscosity-modifying agents thatmay be employed in compositions of the present disclosure may includeany water-soluble or water-dispersible compound that is compatible withthe compositions of the disclosure, such as acrylic polymers,non-acrylic polymers, starch, cellulose-based polymers, non-polymericand polymeric gelling agents, and mixtures thereof.

Methods

Compositions according to the disclosure can be used in methods forremoving color from hair, controlling the removal of color from hair,and/or lightening the color of hair. It is to be understood that“removing” color from hair encompasses any degree or kind of colorremoval. Thus, “removing” color from hair includes removing any amount(e.g. some or all) of color imparted by a particular dye molecule(s)from the hair, or removing any amount (e.g. some or all) of colorimparted by one particular dye molecule(s) from the hair regardless ofwhether any amount of color imparted by another particular dye moleculeremains in the hair. Accordingly, it may be possible to completely orsubstantially remove the color imparted to hair by one or moreparticular dye molecules, control the removal of color imparted to hairby one or more particular dye molecules, or lighten the color impartedto hair by one or more particular dye molecules through variouscombinations and amounts of components in the compositions according tothe disclosure.

In one or more embodiments, the organic salts may be used to removecolor imparted to the hair was imparted by one or more direct dyes whichis(are) either hydrophilic (e.g., cationic) or hydrophobic dyes. Invarious embodiments, the one or more direct dye(s) is(are) hydrophilic.In various embodiments, the one or more direct dye(s) is(are)hydrophobic. In various embodiments, the compositions are particularlyuseful for removing or controlling the removal of semi-permanent haircolor from hair fibers, or lightening the color of hair pre-dyed withsemi-permanent hair color.

Methods according to the disclosure comprise contacting a compositionaccording to the disclosure with hair that has been previously dyed,e.g. by one or more direct dyes, optionally leaving the composition onthe hair for a period of time, and optionally rinsing the compositionfrom the hair. In preferred embodiments, the composition is rinsed fromthe hair with water.

In various embodiments, e.g. where the composition is a rinse-off hairtreatment or mask or serum, the hair may be massaged with thecomposition for a period of time and/or the composition may be left onthe hair for a period of time (“leave-in time”) as desired (e.g., 10,20, 30 seconds or 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 minutes to 20, 30seconds or 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 15 minutes). Optionally, thehair may be heated while the composition is in contact with the hair.For example, the hair may be heated at a temperature ranging from about25° C. to about 60° C., such as with a hair dryer, e.g. a blow dryer ora hood dryer, set at a temperature ranging from about 25° C. to about60° C. The hair may be subsequently be rinsed.

Without being limited by theory, it is believed that methods accordingto the disclosure, e.g. contacting hair previously dyed (“pre-dyedhair”) with one or more direct dyes with a composition containing anorganic salt as described herein, optionally leaving the composition onthe hair for a leave-in time, optionally heating the hair, andoptionally rinsing the composition from the hair, synergisticallyimproves the ease and speed of removing direct dyes from the hair fibersas compared to merely washing the hair with water.

For example, the compositions described herein may be particularlyadvantageous for removing azo direct dyes, (poly)methine dyes such ascyanins, hemicyanins and styryls, carbonyl dyes, azine dyes,nitro(hetero)aryl dyes, tri(hetero)arylmethane dyes, porphyrin dyes,phthalocyanin dyes, and natural direct dyes, alone or as mixtures.Without intending to be limited, the following direct dyes are commonlyused in semi-permanent hair color, which the compositions according tothe disclosure are particularly useful for removing from hair fibers: HCblue 15, hydroxyanthraquinoneaminopropyl methyl morpholiniummethosulfate, Basic violet 2, Disperse violet 1, Disperse red 15,Disperse blue 3, Disperse blue 377, Disperse 99, Solvent violet 13,Basic blue 6, HC blue 16, Basic blue 99, HC blue 14, Basic brown 16,Acid green 25, Acid black 1, HC red 7, HC orange 2,3-Nitro-p-hydroxyethylamino-phenol, Acid red 33, HC violet no. 1,2-Nitro-5-glyceryl methylaniline, 3-Methylamino-4-nitrophenoxyethanol,4-Amino-3-nitrophenol, H yellow 9, Acid red 52, Acid orange 7, Acid red18, HC yellow no. 7, Acid red 92, Acid violet 43, Ext violet 2, Acidgreen 25, or Acid black 1.

Direct Dyes

The methods and compositions of the present disclosure are employed onhair that has been pre-dyed or pre-colored with one or more directdye(s).

Examples of suitable direct dyes that may be mentioned include azodirect dyes; (poly)methine dyes such as cyanins, hemicyanins andstyryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes;tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanin dyes, andnatural direct dyes, alone or as mixtures.

Non-limiting examples of direct dyes include nitro dyes which may bechosen from HC Blue No. 2, HC Blue No. 4, HC Blue No. 5, HC Blue No. 6,HC Blue No. 7, HC Blue No. 8, HC Blue No. 9, HC Blue No. 10, HC Blue No.11, HC Blue No. 12, HC Blue No. 13, HC Blue 15, HC Blue No. 17, HC BrownNo. 1, HC Brown No. 2, HC Green No. 1, HC Orange No. 1, HC Orange No. 2,HC Orange No. 3, HC Orange No. 5, HC Red BN, HC Red No. 1, HC Red No. 3,HC Red No. 7, HC Red No. 8, HC Red No. 9, HC Red No. 10, HC Red No. 11,HC Red No. 13, HC Red No. 54, HC Red No. 14, HC Violet BS, HC Violet No.1, HC Violet No. 2, HC Yellow No. 2, HC Yellow No. 4, HC Yellow No. 5,HC Yellow No. 6, HC Yellow No. 7, HC Yellow No. 8, HC Yellow No. 9, HCYellow No. 10, HC Yellow No. 11, HC Yellow No. 12, HC Yellow No. 13, HCYellow No. 14, HC Yellow No. 15, 2-Amino-6-chloro-4-nitrophenol,picramic acid, 1,2-Diamino-4-nitrobenzol, 1,4-Diamino-2-nitrobenzol,3-Nitro-4-aminophenol, 1-Hydroxy-2-amino-3-nitrobenzol and2-hydroxyethylpicramic acid.

Nitro dyes include non-ionic direct dyes that are typically hydrophobic.Non-limiting examples of hydrophobic direct dyes may be chosen from HCBlue No. 2, HC Blue No. 4, HC Blue No. 5, HC Blue No. 6, HC Blue No. 7,HC Blue No. 8, HC Blue No. 9, HC Blue No. 10, HC Blue No. 11, HC BlueNo. 12, HC Blue No. 13, HC Blue 15, HC Blue No. 17, HC Brown No. 1, HCBrown No. 2, HC Green No. 1, HC Orange No. 1, HC Orange No. 2, HC OrangeNo. 3, HC Orange No. 5, HC Red BN, HC Red No. 1, HC Red No. 3, HC RedNo. 7, HC Red No. 8, HC Red No. 9, HC Red No. 10, HC Red No. 11, HC RedNo. 13, HC Red No. 54, HC Red No. 14, HC Violet BS, HC Violet No. 1, HCViolet No. 2, HC Yellow No. 2, HC Yellow No. 4, HC Yellow No. 5, HCYellow No. 6, HC Yellow No. 7, HC Yellow No. 8, HC Yellow No. 9, HCYellow No. 10, HC Yellow No. 11, HC Yellow No. 12, HC Yellow No. 13, HCYellow No. 14, HC Yellow No. 15.

In an embodiment, the hydrophobic direct dyes of the present disclosureare chosen from HC Blue No. 2, HC Blue No. 4, HC Blue No. 5, HC Blue No.6, HC Blue No. 7, HC Blue No. 8, HC Blue No. 9, HC Blue No. 10, HC BlueNo. 11, HC Blue No. 12, HC Blue No. 13, HC Blue 15, HC Blue No. 17, andmixtures thereof.

Direct dyes may also be chosen from cationic direct dyes. Mention may bemade of the hydrazono cationic dyes of formulas (Va) and (V′a), the azocationic dyes (VIa) and (VI′a) and the diazo cationic dyes (VIIa) below:

Het⁺-C(R^(a))═N—N(R^(b))—Ar, An⁻ (Va) Het⁺-N(R^(a))—N═C(R^(b))—Ar, An⁻(V′a) Het⁺—N═N—Ar, An⁻ (VIa) An⁺—N═N—Ar″, An⁻ (VI′a) andHet⁺—N═N—Ar′—N═N—Ar, An⁻ (VIIa)

in which formulas (Va), (V′a), (VIa), (VI′a) and (VIIa):

-   -   Het⁺ represents a cationic heteroaryl radical, preferably        bearing an endocyclic cationic charge, such as imidazolium,        indolium or pyridinium, optionally substituted preferentially        with one or more (C₁-C₈) alkyl groups such as methyl;    -   Ar⁺ representing an aryl radical, such as phenyl or naphthyl,        bearing an exocyclic cationic charge, preferentially ammonium,        particularly tri(C₁-C₈)alkylammonium such as trimethylammonium;    -   Ar represents an aryl group, especially phenyl, which is        optionally substituted, preferentially with one or more        electron-donating groups such as i) optionally substituted        (C₁-C₈)alkyl, ii) optionally substituted (C₁-C₈)alkoxy, iii)        (di)(C₁-C₈)(alkyl)amino optionally substituted on the alkyl        group(s) with a hydroxyl group, iv) aryl(C₁-C₈)alkylamino, v)        optionally substituted N—(C₁-C₈)alkyl-N-aryl(C₁-C₈)alkylamino or        alternatively Ar represents a julolidine group;    -   Ar′ is an optionally substituted divalent (hetero)arylene group        such as phenylene, particularly para-phenylene, or naphthalene,        which are optionally substituted, preferentially with one or        more groups (C₁-C₈)alkyl, hydroxyl or (C₁-C₈)alkoxy;    -   Ar″ is an optionally substituted (hetero)aryl group such as        phenyl or pyrazolyl, which are optionally substituted,        preferentially with one or more groups (C₁-C₈)alkyl, hydroxyl,        (di)(C₁-C₈)(alkyl)amino, (C₁-C₈)alkoxy or phenyl;    -   R^(a) and R^(b), which may be identical or different, represent        a hydrogen atom or a group (C₁-C₈)alkyl, which is optionally        substituted, preferentially with a hydroxyl group;    -   or alternatively the substituent R^(a) with a substituent of        Het⁺ and/or R_(b) with a substituent of Ar and/or R^(a) with        R_(b) form, together with the atoms that bear them, a        (hetero)cycloalkyl;    -   particularly, R^(a) and R_(b) represent a hydrogen atom or a        group (C₁-C₄)alkyl, which is optionally substituted with a        hydroxyl group; and    -   An⁻ represents an anionic counter-ion such as mesylate or        halide.

In particular, mention may be made of the azo and hydrazono cationicdyes bearing an endocyclic cationic charge of formulae (Va), (V′a) and(VIa) as defined previously. More particularly those of formulae (Va),(V′a) and (VIa) derived from the dyes described in patent applicationsWO 95/15144, WO 95/01772 and EP-714954, which are incorporated herein byreference in their entirety.

In some cases, the cationic part is derived from the followingderivatives:

(Va-1)

(VIa-1)wherein in formulae (Va-1) and (VIa-1):

-   -   R¹ representing a (C₁-C₈) alkyl group such as methyl;    -   R² and R³, which are identical or different, represent a        hydrogen atom or a (C₁-C₄)alkyl group, such as methyl;    -   R⁴ represents a hydrogen atom or an electron-donating group such        as optionally substituted (C₁-C₈)alkyl, optionally substituted        (C₁-C₈)alkoxy, or (di)(C₁-C₈)(alkyl)amino optionally substituted        on the alkyl group(s) with a hydroxyl group; particularly, R⁴ is        a hydrogen atom;    -   Z represents a CH group or a nitrogen atom, preferentially CH;        and    -   An⁻ represents an anionic counter-ion such as mesylate or        halide.

Particularly, the dye of formulae (Va-1) and (VIa-1) is chosen fromBasic Red 51, Basic Yellow 87 and Basic Orange 31 or derivativesthereof:

Non-limiting examples of cationic dyes include Basic Blue 6, Basic Blue7, Basic Blue 9, Basic Blue 26, Basic Blue 41, Basic Blue 99, BasicBrown 4, Basic Brown 16, Basic Brown 17, Natural Brown 7, Basic Green,Basic Orange 31, 1, Basic Red 2, Basic Red 12 Basic Red 22, Basic Red 76Basic Red 51, Basic Violet 1, Basic Violet 2, Basic Violet 3, BasicViolet 10, Basic Violet 14, Basic Yellow 57 and Basic Yellow 87.

Non-limiting examples anionic direct dyes include Acid Black 1, AcidBlue 1, Acid Blue 3, Food Blue 5, Acid Blue 7, Acid Blue 9, Acid Blue74, Acid Orange 3, Acid Orange 6, Acid Orange 7, Acid Orange 10, AcidRed 1, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 50, Acid Red 52,Acid Red 73, Acid Red 87, Acid Red 88, Acid Red 92, Acid Red 155, AcidRed 180, Acid Violet 9, Acid Violet 43, Acid Violet 49, Acid Yellow 1,Acid Yellow 23, Acid Yellow 3, Food Yellow No. 8, D&C Brown No. 1, D&CGreen No. 5, D&C Green No. 8, D&C Orange No. 4, D&C Orange No. 10, D&COrange No. 11, D&C Red No. 21, D&C Red No. 27, D&C Red No. 33, D&CViolet 2, D&C Yellow No. 7, D&C Yellow No. 8, D&C Yellow No. 10, FD&CRed 2, FD&C Red 40, FD&C Red No. 4, FD&C Yellow No. 6, FD&C Blue 1, FoodBlack 1, Food Black 2, Disperse Black 9 and Disperse Violet 1 and theiralkali metal salts such as sodium and/or potassium.

In various embodiments, the direct dye used to pre-color or pre-dye thehair according to the present disclosure is selected from non-ionicdirect dyes, including hydrophobic direct dyes, ionic direct dyes,including cationic direct dyes and anionic direct dyes, and mixturesthereof.

In various embodiments, the direct dye used to pre-color or pre-dye thehair according to the present disclosure is selected from non-ionicdirect dyes, including hydrophobic direct dyes.

In various embodiments, the direct dye used to pre-color or pre-dye thehair according to the present disclosure is selected from ionic directdyes, including cationic direct dyes and anionic direct dyes, andmixtures thereof. In further embodiments, the direct dye used topre-color or pre-dye the hair according to the present disclosure isselected from hydrophilic direct dyes.

In various embodiments, the direct dye used to pre-color or pre-dye thehair according to the present disclosure is selected from hydrophobicdirect dyes. In other embodiments, the direct dye used to pre-color orpre-dye the hair according to the present disclosure is selected fromcationic direct dyes. In yet further embodiments, the direct dye used topre-color or pre-dye the hair according to the present disclosurecomprises a mixture of hydrophobic direct dyes and cationic direct dyes.

In various embodiments, the direct dye used to pre-color or pre-dye thehair according to the present disclosure is selected from the groupconsisting of HC blue 15, hydroxyanthraquinoneaminopropyl methylmorpholinium methosulfate, Basic violet 2, Disperse violet 1, Dispersered 15, Disperse blue 3, Disperse blue 377, Disperse 99, Solvent violet13, Basic blue 6, HC blue 16, Basic blue 99, HC blue 14, Basic brown 16,Acid green 25, Acid black 1, HC red 7, HC orange 2,3-Nitro-p-hydroxyethylaminophenol, Acid red 33, HC violet no. 1,2-Nitro-5-glyceryl methylaniline, 3-Methylamino-4-nitrophenoxyethanol,4-Amino-3-nitrophenol, H yellow 9, Acid red 52, Acid orange 7, Acid red18, HC yellow no. 7, Acid red 92, Acid violet 43, Ext violet 2, Acidgreen 25, Acid black 1 and combinations thereof.

Direct dyes may also be characterized by the partition coefficient (LogP_(ow)) values.

P_(ow) is the octanol/water partition coefficient, which can be definedas the ratio of the concentration of a solute, such as the direct dye inthe present disclosure, in a water-saturated octanolic phase to itsconcentration in an octanol-saturated aqueous phase. The octanol/waterpartition coefficient is typically expressed in Logarithmic form.

There are several existing experimental methods by the Organisation forEconomic Co-operation and Development (OECD) and QuantitativeStructure-Property Relationship (QSPR) models available for Log Powmeasurement or prediction. The experimental methods include: the‘slow-stirring’ method (OECD Test No. 123), the high-performance liquidchromatography (HPLC) method (OECD Test No. 117), and shake flaskmethods (referred to in OECD Test No. 107).

Thus, partition coefficient of a dye may be calculated as follows:Log P _(ow)=Log [(dye concentration in octanol)/(dye concentration inwater)].

The Log P_(ow) value of a direct dye can be positive, negative orneutral. The Log P_(ow) values for some dyes follows in the below table.

DYE NAMES Log P_(ow) HC BLUE NO.2 −0.32 ACID YELLOW 23 −10.17 BASICORANGE 31 −2.31 BASIC RED 51 −1.97 BASIC YELLOW 87 −1.69 ACID YELLOW 3−1.05 HC RED NO.3 −0.42 ACID BLUE 9 −0.32 BASIC BROWN 17 −0.15 BASICYELLOW 57 0.06 HC RED NO.7 0.13 HC ORANGE NO.2 0.133-NITRO-P-HYDROXYETHYLAMINOPHENOL 0.21 ACID RED 33 0.5 HC VIOLET NO 20.608 HC VIOLET NO 1 0.67 2-NITRO-5-GLYCERYL METHYLANILINE 0.89HYDROXYANTHRAQUINONEAMINO-PROPYL 0.89 METHYL MORPHOLINIUM METHOSULFATE3-METHYLAMINO-4-NITROPHENOXYETHANOL 1.13 4-AMINO-3-NITROPHENOL 1.19 HCYELLOW NO.9 1.3 ACID RED 52 1.3 ACID ORANGE 7 1.4 ACID RED18 1.63 BASICBLUE 99 1.88 HC BLUE NO.14 2.09 HC YELLOW NO.7 2.59 DISPERSE VIOLET 1 3ACID RED 92 3 ACID VIOLET 43 3.1 EXT VIOLET 2 3.1 HC BLUE NO. 15 3.47ACID GREEN 25 5.71 ACID BLACK 1 1.2In one or more embodiments the direct dyes used to dye hair may becharacterized by the partition coefficient (Log P_(ow)) values, asdiscussed above.

EXEMPLARY EMBODIMENTS

As discussed above, in some embodiments, the particular uses for thecompositions described herein may be tied to the particular organicsalt, combination of organic salts, or combination of organic salt andsurfactants chosen, as well as to the direct dye that is present oncolor-treated or pre-dyed hair or on hair dyed with a semi-permanent dyethat contains one or more direct dye(s). Thus, the following exemplaryembodiments will be provided to help illustrate such combinations,without being limiting.

Exemplary Compositions

In one or more embodiments, the composition of the present disclosure isa hair color remover comprising:

i. about 0.01 to about 50 wt. % of an organic salt selected from:

-   -   1. an imidazolium-based compound having a structure represented        by Formula (I) below:

-   -   -   wherein R1 and R2 are each independently a linear or            branched alkyl group having 1-16 carbon atoms, and X− is            selected from halides, carboxylates, C₁₋₁₆ fatty acid            carboxylates, phosphate, phosphate derivatives, tosylate,            tosylate derivatives, sulfate and sulfate derivatives,            including alkyl sulfates such as C1-16 sulfates, for example            octyl sulfate;

    -   2. an ammonium-based compound having a structure represented by        Formula (II) below:

-   -   -   wherein R1, R2, R3 and R4 are each independently selected            from saturated or unsaturated, linear, branched or cyclic            groups with the carbon chain length of C₁₋₂₀, which are            optionally substituted by one or more hydroxyl, amino C₁₋₄            radicals, alkylamino, carboxy, carboxylate, carbamide, C₁₋₄            alkoxy, —SO₃H, sulfonate or aryl; and X− is selected from            halides, carboxylates, C₁₋₁₆ fatty acid carboxylates,            phosphate, phosphate derivatives, tosylate, tosylate            derivatives, sulfate and sulfate derivatives; or

    -   3. a combination thereof;

wherein the composition is used for removing one or more direct dye(s)from hair.

In accordance with the present disclosure the above-describedcompositions are to be used on hair that has been pre-dyed with one ormore direct dye(s) which includes, in particular, at least one directdye having a positive Log P_(ow) value and/or at least one hydrophobicdye, in order to remove from hair at least one direct dye having apositive Log P_(ow) value and/or the at least one hydrophobic dye.

In an embodiment, the one or more direct dyes used to color or pre-dyethe hair is HC Blue 15.

In an embodiment, the one or more direct dyes used to color or pre-dyethe hair is hydroxyanthraquinoneaminopropyl methyl morpholiniummethosulfate.

In an embodiment, the one or more direct dyes used to color or pre-dyethe hair is HC Blue 15 and hydroxyanthraquinoneaminopropyl methylmorpholinium methosulfate.

In other embodiments, in accordance with the present disclosure theabove-described compositions are to be used on hair that has beenpre-dyed with one or more direct dye(s) which includes, in particular,at least one direct dye having a positive Log P_(ow) value (or ahydrophobic direct dye) and at least one direct dye having a negativeLog P_(ow) value (or a cationic direct dye).

In an embodiment, the one or more direct dyes used to color or pre-dyethe hair is HC Blue 15 and/or Basic Red 51.

Thus, in an embodiment, the disclosure is related to a composition forremoving one or more direct dyes from hair, the composition containing:

-   -   i. greater than 1 to about 30 wt. % of an organic salt selected        from:        -   1. an imidazolium-based compound having a structure            represented by Formula (I) below:

-   -   -   wherein R1 and R2 are each independently selected from            linear and branched alkyl groups having 1-16 carbon atoms,            and X− is selected from the group consisting of halides,            carboxylates, C₁₋₁₆ fatty acid carboxylates, phosphate,            phosphate derivatives, tosylate, tosylate derivatives,            sulfate and sulfate derivatives;        -   2. an ammonium-based compound having a structure represented            by Formula (II) below:

-   -   -   wherein R1, R2, R3 and R4 are each independently selected            from saturated or unsaturated, linear, branched or cyclic            groups with the carbon chain length of C₁₋₂₀, which are            optionally substituted by one or more hydroxyl, amino C₁₋₄            radicals, alkylamino, carboxy, carboxylate, carbamide, C₁₋₄            alkoxy, —SO₃H, sulfonate or aryl; and X− is selected from            halides, carboxylates, C₁₋₁₆ fatty acid carboxylates,            phosphate, phosphate derivatives, tosylate, tosylate            derivatives, sulfate and sulfate derivatives; or        -   3. a combination thereof; and preferably selected from            butyl-3-methylimidazolium octyl sulfate,            butyl-3-methylimidazolium acetate, ethyl-3-methylimidazolium            ethylsulfate, tributylmethyl ammonium chloride, or            combinations thereof; and

    -   ii. optionally, about 0.01 to about 50% wt. % of a surfactant        selected from an anionic surfactant, a nonionic surfactant, an        amphoteric surfactant and combinations thereof;        wherein the one or more direct dye(s) includes at least one        hydrophobic dye and/or at least one direct dye having a positive        Log P_(ow) value;        wherein all weights are based on the total weight of the        composition.        Exemplary Methods

In various embodiments, the disclosure is directed to methods ofcontacting hair with the compositions described herein in order toremove, from pre-dyed hair, one or more direct dyes comprising at leastone hydrophobic dye and/or at least one direct dye having a positive LogP_(ow) value. Furthermore, the present disclosure is directed to methodsof contacting hair with the compositions described herein in order toremove color or lighten the color of hair that has been colored orpre-dyed with a hair dye containing one or more direct dyes comprisingat least one hydrophobic dye and/or at least one direct dye having apositive Log P_(ow) value. The one or more direct dyes can furthercomprise ionic direct dyes, such as for example cationic or hydrophilicdirect dyes and/or direct dye having a negative Log P_(ow) value, ornonionic direct dyes having a neutral Log P_(ow) value.

Without wishing to be bound to any one theory, it is believed that theionicitities of the direct dyes and/or the types and/or amounts oforganic salt and surfactants can be utilized to control the degreeand/or speed of removal of direct dyes or removal/lightening of colorfrom pre-dyed hair.

In non-limiting exemplary embodiments, composition according to thedisclosure may be combined with other another composition, e.g. arinse-off hair shampoo or conditioner or mask. In such embodiments, themethods would include those steps customary in using shampoos and/orconditioners and/or rinse-off masks or treatments. For example, the hairmay be massaged with the composition for a period of time and/or thecomposition may be left on the hair for a period of time (“leave-intime”) as desired (e.g., 10, 20, 30 seconds or 1, 2, 3, 4, 5, 6, 7, 8, 9or 10 minutes to 20, 30 seconds or 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 15minutes), and optionally heated. The hair is then rinsed after eachtreatment.

Examples

The ingredient amounts in the composition/formulations described beloware expressed in % by weight, based on the total weight of thecomposition, unless otherwise indicated.

Several organic salts were tested for efficacy for color removal ofseveral direct dyes. The organic salts tested are indicated in the tablebelow.

Organic Salts Tested Name Structure Butyl-3-methylimidaz- olium octylsulfate (BMIM octyl sulfate)

Butyl-3-methylimi- dazolium acetate (BMIM OAc)

Ethyl-3-methylimi- dazolium ethylsulfate (EMIM ethylsulfate)

Tributylmethyl ammonium chloride (TBuMA Cl)

Unless otherwise indicated, the formulations described contained theactive ingredients listed with the balance made up of water.

Unless otherwise indicated, hair swatches were all treated using thesame protocol. Specifically, 2 g dyed hair swatches are soaked in 80 gtreatment solution in water for 30 minutes at 40° C., then the treatedhair swatches are then shampooed/washed once (rinsing step) andblow-dried for evaluation.

Unless otherwise indicated, color removal performance is measured usingCIE L* a* b* coordinates. ΔE is used to describe the color differenceand is defined by the following equation:ΔE* _(ab)=√{square root over ((L* ₂ −L* ₁)²+(a* ₂ −a* ₁)²+(b* ₂ −b*₁)²)}where, L1*, a₁; b₁ are measured on freshly dyed hair L₂*, a₂, b₂ aremeasured on the dyed hair treated by color remover systems. The higherΔE values, the more efficient the color removal.

Example 1—Removal of HC Blue 15 Using Organic Salts

HC Blue 15 contains multi-aromatic rings and has the structure below.The Log P_(ow) value around 3.47.

Hair swatches dyed with HC Blue 15 were treated with the organic saltsat varying concentrations using the protocol described above. Theresulting ΔE are shown in the below table, as well as in FIG. 1.

ΔE Values ΔE Concentration BMIM of Octyl BMIM TBuMA EMIM Organic saltsulfate OAc Cl ethylsulfate 0% 6.0 (control) 1% 1.3 3.6 1.1 5% 18.4 1.12.1 10%  32.2 5.6 1.8 1.5 25%  8.6 32.8 9.3 50%  36.14 26.8

As seen from the FIG. 1, the organic salts are capable of enhancing theremoval of dye. Starting at about 5% of the organic salt, the ΔE valueincreased significantly for BMIM octyl sulfate, indicating significantremoval of the dye. For the other organic salts, a significant increasein the ΔE values was observed starting at about 25% of the organic salt.Thus, more color, i.e., a greater amount of dye is removed as theconcentration of the organic salt was increased. Moreover, thesignificantly higher ΔE values after treatment of the hair with organicsalt solutions were accompanied by removal of color from or lighteningof the color of the hair as visually seen by the naked eye.

Example 2—Removal of Basic Red 51

Hair swatches dyed with Basic Red 51 were treated with BMIM octylsulfateand TBuMA Cl, each at 10% concentration using the protocol describedabove. Basic Red 51 contains a quaternary moiety and has the structurebelow. The Log P_(ow) value around −1.97.

The resulting ΔE are in FIG. 2. For the treatment with water alone(control), the ΔE value was 5.3. For the treatment with BMIM octylsulfate, the ΔE value was 22.2 and for the treatment with TBuMA Cl, theΔE value was 23.1. As shown by the results, BMIM octylsulfate and TBuMACl can remove Basic Red 51 from hair fibers.

Example 3—Removal of Hydroxyanthraquinoneaminopropyl Methyl MorpholiniumMethosulfate

Hair swatches dyed with hydroxyanthraquinoneaminopropyl methylmorpholinium methosulfate were treated with BMIM octylsulfate at 10%concentration using the protocol described above.Hydroxyanthraquinoneaminopropyl methyl morpholinium methosulfate has thestructure below, and a Log P_(ow) value around 2.89.

The resulting ΔE values are in FIG. 3. For the treatment with wateralone (control), the ΔE value was 2.9. For the treatment with BMIM octylsulfate, the ΔE value was 39.1. As shown by the results, BMIMoctylsulfate can remove hydroxyanthraquinoneaminopropyl methylmorpholinium methosulfate from hair fibers.

The terms “comprising,” “having,” and “including” are used in theiropen, non-limiting sense.

The terms “a” and “the” are understood to encompass the plural as wellas the singular.

The compositions and methods of the present disclosure can comprise,consist of, or consist essentially of the essential elements andlimitations of the disclosure described herein, as well as anyadditional or optional ingredients, components, or limitations describedherein or otherwise useful.

All percentages, parts and ratios herein are based upon the total weightof the compositions of the present disclosure, unless otherwiseindicated.

All ranges and values disclosed herein are inclusive and combinable. Forexamples, any value or point described herein that falls within a rangedescribed herein can serve as a minimum or maximum value to derive asub-range, etc. Furthermore, all ranges provided are meant to includeevery specific range within, and combination of sub ranges between, thegiven ranges. Thus, a range from 1-5, includes specifically 1, 2, 3, 4and 5, as well as sub ranges such as 2-5, 3-5, 2-3, 2-4, 1-4, etc.

Other than in the operating examples, or where otherwise indicated, allnumbers expressing quantities of ingredients and/or reaction conditionsare to be understood as being modified in all instances by the term“about” which can encompass +/−10%, +/−8%, +/−6%, +/−5%, +/−4%, +/−3%,+/−2%, +/−1%, or +/−0.5%.

All numbers expressing pH values are to be understood as being modifiedin all instances by the term “about” which encompasses up to +/−3%. Asused herein, the expression “at least one” is interchangeable with theexpression “one or more” and thus includes individual components as wellas mixtures/combinations.

The term “active material” as used herein with respect to the percentamount of an ingredient or raw material, refers to 100% activity of theingredient or raw material.

The terms “a,” “an,” and “the” are understood to encompass the plural aswell as the singular. Thus, the term “a mixture thereof” also relates to“mixtures thereof.

“Substituted,” as used herein, means comprising at least onesubstituent. Non-limiting examples of substituents include atoms, suchas oxygen atoms and nitrogen atoms, as well as functional groups, suchas hydroxyl groups, ether groups, alkoxy groups, acyloxyalkyl groups,oxyalkylene groups, polyoxyalkylene groups, carboxylic acid groups,amine groups, acylamino groups, amide groups, haLogen containing groups,ester groups, thiol groups, sulphonate groups, thiosulphate groups,siloxane groups, and polysiloxane groups. The substituent(s) may befurther substituted.

The term “neutralized” as used herein is intended to mean that the3-butoxypropylamine is protonated with a H₊ (proton) coming from thediacid(s).

The term “substantially free of (a component)” as defined herein meansthat the system or composition contains no appreciable amount of thecomponent, for example, no more than about 1% by weight, no more thanabout 0.5% by weight, or no more than about 0.3% by weight, such as nomore than about 0.1% by weight, based on the weight of the composition.

The term “free” or “completely free of (a component)” as defined hereinmeans that the composition does not contain the component in anymeasurable degree by standard means.

Likewise, the term “a salt thereof” also relates to “salts thereof.”Thus, where the disclosure refers to “an element selected from the groupconsisting of A, B, C, D, E, F, a salt thereof, and a mixture thereof,”it indicates that that one or more of A, B, C, D, and F may be included,one or more of a salt of A, a salt of B, a salt of C, a salt of D, asalt of E, and a salt of F may be included, or a mixture of any two ofA, B, C, D, E, F, a salt of A, a salt of B, a salt of C, a salt of D, asalt of E, and a salt of F may be included.

The salts referred to throughout the disclosure may include salts havinga counter-ion such as an alkali metal, alkaline earth metal, or ammoniumcounter-ion. This list of counter-ions, however, is non-limiting.

The expression “inclusive” for a range of concentrations means that thelimits of the range are included in the defined interval.

All components and elements positively set forth in this disclosure canbe negatively excluded from the claims. In other words, the compositionsof the instant disclosure can be free or essentially free of allcomponents and elements positively recited throughout the instantdisclosure.

All publications and patent applications cited in this specification areherein incorporated by reference, and for any and all purposes, as ifeach individual publication or patent application were specifically andindividually indicated to be incorporated by reference. In the event ofan inconsistency between the present disclosure and any publications orpatent application incorporated herein by reference, the presentdisclosure controls.

What is claimed is:
 1. A method for removing one or more direct dyesfrom hair, the method comprising: a. contacting the hair with acomposition comprising: i. at least one organic salt chosen from: animidazolium-based compound of Formula (I):

wherein  R1 and R2 are each independently a linear or branched alkylgroup having 1-16 carbon atoms, and  X⁻ is chosen from halides,carboxylates, C1-16 fatty acid carboxylates, phosphates, phosphatederivatives, tosylates, tosylate derivatives, sulfates, or sulfatederivatives; an ammonium-based compound of Formula (II):

wherein  R1, R2, R3 and R4 are each independently a saturated orunsaturated, linear, branched or cyclic group with a carbon chain lengthof C₁₋₂₀, optionally substituted with one or more hydroxyl, amino C₁₋₄radicals, alkylamino, carboxy, carboxylate, carbamide, C₁₋₄ alkoxy,—SO₃H, sulfonate or aryl; and  X⁻ is chosen from halides, carboxylates,C1-16 fatty acid carboxylates, phosphates, phosphate derivatives,tosylates, tosylate derivatives, sulfates, or sulfate derivatives; orcombinations thereof; and b. rinsing the composition from the hair. 2.The method of claim 1, wherein: R1, R2, R3, and R4 of Formula (II) areeach independently a linear or branched alkyl group with a carbon chainlength of C₁₋₂₀; and X⁻ of Formula (II) is chosen from carboxylates,C₁₋₁₆ fatty acid carboxylates, sulfates, or sulfate derivatives,including alkyl sulfates.
 3. The method of claim 1, wherein the compoundof Formula (II) is chosen from:

wherein X⁻ is chosen from halides, carboxylates, C₁₋₁₆ fatty acidcarboxylates, phosphates, phosphate derivatives, tosylates, tosylatederivatives, sulfates, or sulfate derivatives.
 4. The method of claim 1,wherein the at least one organic salt is chosen from1-butyl-3-methylimidazolium octyl sulfate, 1-butyl-3-methylimidazoliumacetate, 1-ethyl-3-methylimidazolium ethylsulfate, 1-ethyl-3-ethylimidazolium acetate, 1-ethyl-3-methylimidazolium tosylate, orcombinations thereof.
 5. The method of claim 1, wherein the at least oneorganic salt is chosen from an ammonium-based compound comprising atributylmethyl ammonium salt.
 6. The method of claim 1, wherein the atleast one organic salt is chosen from an imidazolium-based compound ofFormula (I) in ionic liquid form.
 7. The method of claim 1, wherein theat least one organic salt is chosen from an ammonium-based compound ofFormula (II) in ionic liquid form.
 8. The method of claim 1, wherein theat least one organic salt is present in the composition at aconcentration of greater than about 1% by weight, based on the totalweight of the composition.
 9. The method of claim 1, wherein thecomposition further comprises a surfactant.
 10. The method of claim 1,wherein the one or more direct dyes is chosen from: direct dyes having apositive Log P_(ow) value, direct dyes having a negative Log P_(ow)value, direct dyes having a neutral Log P_(ow) value, or combinationsthereof.
 11. The method of claim 10, wherein the direct dyes having apositive Log P_(ow) value are chosen from hydrophobic direct dyesincluding HC blue 15, hydroxyanthraquinoneaminopropyl methylmorpholinium methosulfate, Basic violet 2, Disperse violet 1, Dispersered 15, Disperse blue 3, Disperse blue 377, Disperse 99, Solvent violet13, Basic blue 6, HC blue 16, Basic blue 99, HC blue 14, Basic brown 16,Acid green 25, Acid black 1, HC red 7, HC orange 2,3-Nitro-p-hydroxyethylaminophenol, Acid red 33, HC violet no. 1,2-Nitro-5-glyceryl methylaniline, 3-Methylamino-4-nitrophenoxyethanol,4-Amino-3-nitrophenol, H yellow 9, Acid red 52, Acid orange 7, Acid red18, HC yellow no. 7, Acid red 92, Acid violet 43, Ext violet 2, Acidgreen 25, Acid black 1, or combinations thereof.
 12. The method of claim10, wherein the direct dyes having a negative Log P_(ow) value arechosen from cationic direct dyes including basic orange 31, basic red51, basic yellow 57, HC blue no. 2, Acid yellow 23, Basic orange 31,Basic yellow 87, Acid yellow 3, HC Red 3, Acid blue 9, Basic brown 17,or combinations thereof.
 13. The method of claim 1, wherein one or moredirect dyes is removed from the hair or the hair is lightened followingstep (b).
 14. The method of claim 1, wherein: the one or more directdyes is chosen from direct dyes having a positive Log P_(ow) value, andthe organic salt is chosen from: an imidazolium-based compound chosenfrom butyl-3-methylimidazolium octyl sulfate, butyl-3-methylimidazoliumacetate, ethyl-3-methylimidazolium ethylsulfate, 1-ethyl-3-ethylimidazolium acetate, or 1-ethyl-3-methylimidazolium tosylate,tributylmethyl ammonium chloride, or combinations thereof.
 15. Themethod of claim 1, wherein: the one or more direct dyes is chosen fromdirect dyes having a negative Log P_(ow) value, and the organic salt ischosen from 1-butyl-3-methylimidazolium octyl sulfate, tributylmethylammonium chloride, or a combination thereof.
 16. A method for removingcolor from hair, controlling the removal of color from hair, orlightening the color of hair, the method comprising: a. contacting thehair with a composition comprising: i. at least one organic salt chosenfrom: an imidazolium-based compound of Formula (I):

wherein R1 and R2 are each independently a linear or branched alkylgroup having 1-16 carbon atoms, and X⁻ is chosen from halides,carboxylates, C1-16 fatty acid carboxylates, phosphates, phosphatederivatives, tosylates, tosylate derivatives, sulfates, or sulfatederivatives; an ammonium-based compound of Formula (II):

wherein R1, R2, R3 and R4 are each independently a saturated orunsaturated, linear, branched or cyclic group with a carbon chain lengthof C₁₋₂₀, optionally substituted with one or more hydroxyl, amino C₁₋₄radicals, alkylamino, carboxy, carboxylate, carbamide, C₁₋₄alkoxy,—SO₃H, sulfonate, or aryl; and X⁻ is chosen from halides, carboxylates,C₁₋₁₆ fatty acid carboxylates, phosphates, phosphate derivatives,tosylates, tosylate derivatives, sulfates, or sulfate derivatives; orcombinations thereof; and b. rinsing the composition from the hair;wherein the hair has been pre-dyed with one or more direct dyes.
 17. Themethod of claim 16, wherein R1, R2, R3, and R4 of Formula (II) are eachindependently a linear or branched alkyl group with a carbon chainlength of C₁₋₂₀, and X⁻ of Formula (II) is chosen from carboxylates,C₁₋₁₆ fatty acid carboxylates, sulfates, or sulfate derivatives,including alkyl sulfates.
 18. The method of claim 16, wherein theammonium-based compound of Formula (II) is chosen from:

wherein X⁻ is chosen from halides, carboxylates, C1-16 fatty acidcarboxylates, phosphates, phosphate derivatives, tosylates, tosylatederivatives, sulfates, or sulfate derivatives.
 19. The method of claim16, wherein the at least one organic salt is chosen from: animidazolium-based compound chosen from 1-butyl-3-methylimidazolium octylsulfate, 1-butyl-3-methylimidazolium acetate,1-ethyl-3-methylimidazolium ethylsulfate, 1-ethyl-3-ethyl imidazoliumacetate, or 1-ethyl-3-methylimidazolium tosylate; an ammonium-basedcompound chosen from tributylmethyl ammonium salts; or combinationsthereof.
 20. The method of claim 16, wherein the one or more direct dyesare chosen from: (1) direct dyes having a positive Log P_(ow) valuechosen from HC blue 15, hydroxyanthraquinoneaminopropyl methylmorpholinium methosulfate, Basic violet 2, Disperse violet 1, Dispersered 15, Disperse blue 3, Disperse blue 377, Disperse 99, Solvent violet13, Basic blue 6, HC blue 16, Basic blue 99, HC blue 14, Basic brown 16,Acid green 25, Acid black 1, HC red 7, HC orange 2,3-Nitro-p-hydroxyethylaminophenol, Acid red 33, HC violet no. 1,2-Nitro-5-glyceryl methylaniline, 3-Methylamino-4-nitrophenoxyethanol,4-Amino-3-nitrophenol, H yellow 9, Acid red 52, Acid orange 7, Acid red18, HC yellow no. 7, Acid red 92, Acid violet 43, Ext violet 2, Acidgreen 25, Acid black 1; or (2) direct dyes having a negative Log P_(ow)value chosen from basic orange 31, basic red 51, basic yellow 57, HCblue no. 2, Acid yellow 23, Basic orange 31, Basic yellow 87, Acidyellow 3, HC Red 3, Acid blue 9, Basic brown 17; or (3) combinationsthereof.
 21. A composition for removing one or more direct dyes fromhair, the composition comprising at least one organic salt chosen from:an imidazolium-based compound chosen from 1-butyl-3-methylimidazoliumoctyl sulfate, 1-butyl-3-methylimidazolium acetate,1-ethyl-3-methylimidazolium ethylsulfate, 1-ethyl-3-ethyl imidazoliumacetate, or 1-ethyl-3-methylimidazolium tosylate; an ammonium-basedcompound chosen from tributylmethyl ammonium salts; or combinationsthereof; wherein the at least one organic salt is present in thecomposition at a concentration effective to remove one or more directdyes from the hair, based on the total weight of the composition. 22.The composition of claim 21, wherein the one or more direct dyes ischosen from: (1) direct dyes having a positive Log P_(ow) value chosenfrom HC blue 15, hydroxyanthraquinoneaminopropyl methyl morpholiniummethosulfate, Basic violet 2, Disperse violet 1, Disperse red 15,Disperse blue 3, Disperse blue 377, Disperse 99, Solvent violet 13,Basic blue 6, HC blue 16, Basic blue 99, HC blue 14, Basic brown 16,Acid green 25, Acid black 1, HC red 7, HC orange 2,3-Nitro-p-hydroxyethylaminophenol, Acid red 33, HC violet no. 1,2-Nitro-5-glyceryl methylaniline, 3-Methylamino-4-nitrophenoxyethanol,4-Amino-3-nitrophenol, H yellow 9, Acid red 52, Acid orange 7, Acid red18, HC yellow no. 7, Acid red 92, Acid violet 43, Ext violet 2, Acidgreen 25, or Acid black 1; (2) direct dyes having a negative Log P_(ow)value chosen from basic orange 31, basic red 51, basic yellow 57, HCblue no. 2, Acid yellow 23, Basic orange 31, Basic yellow 87, Acidyellow 3, HC Red 3, Acid blue 9, or Basic brown 17; or (3) combinationsthereof.